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1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione is a complex heterocyclic compound characterized by a unique fused ring system. It features a pyrazine ring fused to an oxazine ring and a pyrido ring, with additional benzyloxy and methyl groups attached at specific positions. This distinctive structure endows the compound with potential for specific biological activities or target binding properties, making it a promising candidate for applications in medicinal chemistry and drug discovery.

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  • (4R,12aS)-7-(Benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione

    Cas No: 1206102-09-1

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  • 1206102-09-1 Structure

  • Basic information

    1. Product Name: (4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione
    2. Synonyms: (4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione;Dolutegravir interMediate;(4R,12aS)-7-(Benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione;2H-Pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione, 3,4,12,12a-tetrahydro-4-methyl-7-(phenylmethoxy)-, (4R,12aS)-;Intermediate of Dolutegravir
    3. CAS NO:1206102-09-1
    4. Molecular Formula: C19H20N2O4
    5. Molecular Weight: 340.3731
    6. EINECS: -0
    7. Product Categories: N/A
    8. Mol File: 1206102-09-1.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione(CAS DataBase Reference)
    10. NIST Chemistry Reference: (4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione(1206102-09-1)
    11. EPA Substance Registry System: (4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione(1206102-09-1)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1206102-09-1(Hazardous Substances Data)

1206102-09-1 Usage

Uses

Used in Medicinal Chemistry:
(4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione is used as a potential lead compound for the development of new drugs due to its unique structure and potential biological activities.
Used in Drug Discovery:
In the field of drug discovery, (4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione serves as a valuable starting point for the identification and optimization of novel therapeutic agents. Its specific structural features may enable selective binding to molecular targets, leading to the development of targeted treatments for various diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 1206102-09-1 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,2,0,6,1,0 and 2 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1206102-09:
(9*1)+(8*2)+(7*0)+(6*6)+(5*1)+(4*0)+(3*2)+(2*0)+(1*9)=81
81 % 10 = 1
So 1206102-09-1 is a valid CAS Registry Number.

1206102-09-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2H-?Pyrido[1',?2':4,?5]?pyrazino[2,?1-?b]?[1,?3]?oxazine-?6,?8-?dione, 3,?4,?12,?12a-?tetrahydro-?4-?methyl-?7-?(phenylmethoxy)?-?, (4R,?12aS)?-

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1206102-09-1 SDS

1206102-09-1Synthetic route

(R)-3-amino-1-butanol
61477-40-5

(R)-3-amino-1-butanol

methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate
1206102-08-0

methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
With acetic acid In toluene at 90℃; for 3.5h;96%
With acetic acid In toluene at 90℃; for 2.5h; Product distribution / selectivity;83%
With acetic acid In methanol; toluene at 90℃; for 2.5h; Reagent/catalyst; Temperature;83%
With acetic acid In toluene at 90℃; for 2h; diastereoselective reaction;80%
2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one
1206102-04-6

2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.5 h / 30 °C
2.1: rhodium(III) chloride hydrate; sodium periodate; sulfuric acid / water; acetonitrile / 3.5 h / 20 °C
2.2: 1.5 h / 25 °C
3.1: ethanol / 8.5 h / 65 - 80 °C
4.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
5.1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
6.1: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: triethylamine; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.5 h / 30 °C
2.1: rhodium(III) chloride hydrate; sodium periodate; sulfuric acid / water; acetonitrile / 3.5 h / 20 °C
2.2: 1.5 h / 25 °C
3.1: ethanol / 8.5 h / 65 - 80 °C
4.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
5.1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
6.1: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 3 steps
1: methanesulfonyl chloride
2: ruthenium trichloride; sodium periodate
3: sodium periodate
View Scheme
Multi-step reaction with 7 steps
1.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1 h / 20 °C / Large scale
1.2: 1 h / Large scale
2.1: ruthenium trichloride; sodium periodate; sulfuric acid / acetonitrile; water / 20 °C / Large scale
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite / acetonitrile; water; ethyl acetate / 20 °C / Large scale
4.1: ethanol / 3.5 h / 65 - 75 °C / Large scale
5.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 30 °C / Large scale
6.1: sodium periodate; acetic anhydride / acetonitrile; water / 30 °C / Large scale
7.1: acetic acid / toluene / 2 h / 90 °C
View Scheme
C20H16O3
1229006-11-4

C20H16O3

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: rhodium(III) chloride hydrate; sodium periodate; sulfuric acid / water; acetonitrile / 3.5 h / 20 °C
1.2: 1.5 h / 25 °C
2.1: ethanol / 8.5 h / 65 - 80 °C
3.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
4.1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
5.1: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: rhodium(III) chloride hydrate; sodium periodate; sulfuric acid / water; acetonitrile / 3.5 h / 20 °C
1.2: 1.5 h / 25 °C
2.1: ethanol / 8.5 h / 65 - 80 °C
3.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
4.1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
5.1: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: ruthenium trichloride; sodium periodate
2: sodium periodate
View Scheme
4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid
119736-16-2

4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 8.5 h / 65 - 80 °C
2: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
3: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
4: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 4 steps
1: ethanol / 8.5 h / 65 - 80 °C
2: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
3: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
4: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 4 steps
1: ethanol / 1 h / Reflux
2: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one / 5 h / 20 °C
3: sodium periodate / methanol; water / 1 h / 20 °C
4: acetic acid / toluene / 3.5 h / 90 °C
View Scheme
Multi-step reaction with 4 steps
1: ethanol / 3.5 h / 65 - 75 °C / Large scale
2: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 30 °C / Large scale
3: sodium periodate; acetic anhydride / acetonitrile; water / 30 °C / Large scale
4: acetic acid / toluene / 2 h / 90 °C
View Scheme
1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid
1206102-06-8

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
2: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
3: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
2: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
3: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one / 5 h / 20 °C
2: sodium periodate / methanol; water / 1 h / 20 °C
3: acetic acid / toluene / 3.5 h / 90 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 30 °C / Large scale
2: sodium periodate; acetic anhydride / acetonitrile; water / 30 °C / Large scale
3: acetic acid / toluene / 2 h / 90 °C
View Scheme
1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester
1206102-07-9

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
2: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium periodate / methanol; water / 1 h / 20 °C
2: acetic acid / toluene / 3.5 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium periodate; acetic anhydride / acetonitrile; water / 30 °C / Large scale
2: acetic acid / toluene / 2 h / 90 °C
View Scheme
Maltol
118-71-8

Maltol

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: potassium carbonate / acetonitrile / 5 h / 13 - 80 °C / Large scale
2: bromobenzene; selenium(IV) oxide / 13 h / 140 °C / Dean-Stark
3: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
4: ethanol / 8.5 h / 65 - 80 °C
5: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
6: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
7: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate / acetonitrile / 5 h / 13 - 80 °C / Large scale
2: bromobenzene; selenium(IV) oxide / 13 h / 140 °C / Dean-Stark
3: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
4: ethanol / 8.5 h / 65 - 80 °C
5: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
6: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
7: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate / acetonitrile / 5 h / 13 - 80 °C / Large scale
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -60 °C
2.2: 1 h / -60 °C
3.1: triethylamine; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.5 h / 30 °C
4.1: rhodium(III) chloride hydrate; sodium periodate; sulfuric acid / water; acetonitrile / 3.5 h / 20 °C
4.2: 1.5 h / 25 °C
5.1: ethanol / 8.5 h / 65 - 80 °C
6.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
7.1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
8.1: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde
500371-01-7

3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
2: ethanol / 8.5 h / 65 - 80 °C
3: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
4: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
5: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
2: ethanol / 8.5 h / 65 - 80 °C
3: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
4: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
5: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite / acetonitrile; water; ethyl acetate / 20 °C / Large scale
2: ethanol / 3.5 h / 65 - 75 °C / Large scale
3: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 30 °C / Large scale
4: sodium periodate; acetic anhydride / acetonitrile; water / 30 °C / Large scale
5: acetic acid / toluene / 2 h / 90 °C
View Scheme
benzyl bromide
100-39-0

benzyl bromide

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: potassium carbonate / acetonitrile / 5 h / 13 - 80 °C / Large scale
2: bromobenzene; selenium(IV) oxide / 13 h / 140 °C / Dean-Stark
3: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
4: ethanol / 8.5 h / 65 - 80 °C
5: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
6: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
7: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate / acetonitrile / 5 h / 13 - 80 °C / Large scale
2: bromobenzene; selenium(IV) oxide / 13 h / 140 °C / Dean-Stark
3: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
4: ethanol / 8.5 h / 65 - 80 °C
5: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
6: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
7: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate / acetonitrile / 5 h / 13 - 80 °C / Large scale
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -60 °C
2.2: 1 h / -60 °C
3.1: triethylamine; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.5 h / 30 °C
4.1: rhodium(III) chloride hydrate; sodium periodate; sulfuric acid / water; acetonitrile / 3.5 h / 20 °C
4.2: 1.5 h / 25 °C
5.1: ethanol / 8.5 h / 65 - 80 °C
6.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
7.1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
8.1: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
3-O-benzylmaltol
61049-69-2

3-O-benzylmaltol

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: bromobenzene; selenium(IV) oxide / 13 h / 140 °C / Dean-Stark
2: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
3: ethanol / 8.5 h / 65 - 80 °C
4: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
5: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
6: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 6 steps
1: bromobenzene; selenium(IV) oxide / 13 h / 140 °C / Dean-Stark
2: sodium chlorite; aminosulfonic acid / water; acetone / 0.67 h / 20 °C / Cooling with ice
3: ethanol / 8.5 h / 65 - 80 °C
4: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
5: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
6: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -60 °C
1.2: 1 h / -60 °C
2.1: triethylamine; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.5 h / 30 °C
3.1: rhodium(III) chloride hydrate; sodium periodate; sulfuric acid / water; acetonitrile / 3.5 h / 20 °C
3.2: 1.5 h / 25 °C
4.1: ethanol / 8.5 h / 65 - 80 °C
5.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 28 - 35 °C / Large scale
6.1: sodium periodate; sulfuric acid / water; acetonitrile / 1 h / 14 - 17 °C
7.1: acetic acid / methanol; toluene / 2.5 h / 90 °C
View Scheme
benzyl chloride
100-44-7

benzyl chloride

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium carbonate / methanol / 1 h / Reflux
2: periodic acid; chromium(VI) oxide / acetonitrile / 1.5 h / 20 °C
3: ethanol / 1 h / Reflux
4: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one / 5 h / 20 °C
5: sodium periodate / methanol; water / 1 h / 20 °C
6: acetic acid / toluene / 3.5 h / 90 °C
View Scheme
(R)-3-amino-1-butanol
61477-40-5

(R)-3-amino-1-butanol

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester
1206102-07-9

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Stage #1: 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester With sodium periodate
Stage #2: (R)-3-amino-1-butanol
C21H20O6S

C21H20O6S

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene
2: ruthenium trichloride; sodium periodate
3: sodium periodate
View Scheme
2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one
1206102-05-7

2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: ruthenium trichloride; sodium periodate; sulfuric acid / acetonitrile; water / 20 °C / Large scale
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite / acetonitrile; water; ethyl acetate / 20 °C / Large scale
3: ethanol / 3.5 h / 65 - 75 °C / Large scale
4: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 30 °C / Large scale
5: sodium periodate; acetic anhydride / acetonitrile; water / 30 °C / Large scale
6: acetic acid / toluene / 2 h / 90 °C
View Scheme
(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

(4R,12aS)-7-(benzyloxy)-9-bromo-4-methyl-3,4,12,12atetrahydro-2H-pyrido [1′,2′:4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-10-4

(4R,12aS)-7-(benzyloxy)-9-bromo-4-methyl-3,4,12,12atetrahydro-2H-pyrido [1′,2′:4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione

Conditions
ConditionsYield
With N-Bromosuccinimide In 1-methyl-pyrrolidin-2-one at 20℃; for 2h; Product distribution / selectivity;89%
With N-Bromosuccinimide In 1-methyl-pyrrolidin-2-one; water at 5 - 20℃; for 4h; Solvent; Temperature;89%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1.5h;86%
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.5h; Large scale;85%
With N-Bromosuccinimide
(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

dolutegravir

dolutegravir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / 1-methyl-pyrrolidin-2-one; water / 4 h / 5 - 20 °C
2: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 5.5 h / 90 °C
3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 2.5 h
View Scheme
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / dichloromethane / 0.5 h / 20 °C / Large scale
2: tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 5 h / 90 °C / Large scale
3: hydrogen; 5%-palladium/activated carbon / tetrahydrofuran; water / 2 h / 40 °C
View Scheme
(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

(4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1′,2′:4,5]pyrazino-[2,1-b][1,3]oxazine-9-carboxamide sodium salt
1051375-19-9

(4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1′,2′:4,5]pyrazino-[2,1-b][1,3]oxazine-9-carboxamide sodium salt

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / 1-methyl-pyrrolidin-2-one; water / 4 h / 5 - 20 °C
2: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 5.5 h / 90 °C
3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 2.5 h
4: sodium hydroxide / ethanol / 80 °C
View Scheme
Multi-step reaction with 3 steps
1.1: N-Bromosuccinimide
2.1: tetrakis(triphenylphosphine) palladium(0)
3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran; methanol / 2.5 h
3.2: 80 °C
View Scheme
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / dichloromethane / 0.5 h / 20 °C / Large scale
2: tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 5 h / 90 °C / Large scale
3: hydrogen; 5%-palladium/activated carbon / tetrahydrofuran; water / 2 h / 40 °C
4: sodium hydroxide / water; ethanol / 3 h / 25 °C
View Scheme
(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione
1206102-09-1

(4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione

(4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1′,2’:4,5]-pyrazino[2,1-b][1,3]oxazine-9-carboxamide
1206102-11-5

(4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1′,2’:4,5]-pyrazino[2,1-b][1,3]oxazine-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide
2: tetrakis(triphenylphosphine) palladium(0)
View Scheme
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / dichloromethane / 0.5 h / 20 °C / Large scale
2: tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 5 h / 90 °C / Large scale
View Scheme

1206102-09-1Relevant articles and documents

Practical and Scalable Synthetic Method for Preparation of Dolutegravir Sodium: Improvement of a Synthetic Route for Large-Scale Synthesis

Aoyama, Yasunori,Hakogi, Toshikazu,Fukui, Yuki,Yamada, Daisuke,Ooyama, Takao,Nishino, Yutaka,Shinomoto, Shoji,Nagai, Masahiko,Miyake, Naoki,Taoda, Yoshiyuki,Yoshida, Hiroshi,Yasukata, Tatsuro

, p. 558 - 564 (2019/04/30)

A practical and scalable synthetic method to obtain dolutegravir sodium (1) was established starting from the readily accessible material maltol (2). This synthetic method includes a scalable oxidation process of maltol and palladium-catalyzed amidation for introduction of an amide moiety, leading to a practical manufacturing method in short synthetic steps. The synthetic method demonstrated herein enables multikilogram scale manufacturing of 1 of high purity.

Practical Synthetic Method for the Preparation of Pyrone Diesters: An Efficient Synthetic Route for the Synthesis of Dolutegravir Sodium

Yasukata, Tatsuro,Masui, Moriyasu,Ikarashi, Fumiya,Okamoto, Kazuya,Kurita, Takanori,Nagai, Masahiko,Sugata, Yoshihide,Miyake, Naoki,Hara, Shinichiro,Adachi, You,Sumino, Yukihito

, p. 565 - 570 (2019/03/26)

A highly efficient and practical synthetic method for the preparation of pyrone diesters was established. The pyrone diester 3c can be prepared from readily available starting materials on a multihundred gram scale. The pyrone diester 3c can easily be converted to dolutegravir sodium (1). The synthetic route demonstrated herein provides an efficient and atom-economical synthetic method for preparing this potent anti-HIV agent.

Improved method for synthesizing dolutegravir

-

, (2019/03/30)

The invention relates to an improved method for synthesizing dolutegravir and belongs to the field of medicinal chemistry. The method takes maltol (compound 1) as a raw material, and a target is synthesized by the following route. The process raw material is cheap and easy to obtain, a reaction solvent can be recycled, the post-treatment operation is simple, the yield and the purity are high, especially the carbamoylation and debenzylation reaction are carried out in one step, the synthesis route is simplified, the cost is reduced, and the large-scale industrial production is facilitated.

Intermediate of these pyridonecarboxylic carbamoylalkanoic and HIV integrase inhibitor

-

, (2016/10/07)

A synthesis approach providing an early ring attachment via a bromination to compound I-I yielding compound II-II: whereby a final product such as AA: can be synthesized. In particular, the 2,4-difluorophenyl-containing sidechain is attached before creation of the additional ring Q.

PROCESSES AND INTERMEDIATES FOR CARBAMOYLPYRIDONE HIV INTEGRASE INHIBITORS

-

Page/Page column 18, (2010/07/02)

Processes are provided which create an aldehyde methylene, or hydrated or hemiacetal methylene attached to a heteroatom of a 6 membered ring without going through an olefinic group and without the necessity of using an osmium reagent. In particular, a comopound of formula (I) can be produced from (II) and avoid the use of an allyl amine: (formulae I and II) where R, P 1 P3, R3 and Rx are as described herein.

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