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654671-77-9

Basic Information
CAS No.: 654671-77-9
Name: Sitagliptin phosphate monohydrate
Article Data: 6
Cas Database
Molecular Structure:
Molecular Structure of 654671-77-9 (Sitagliptin phosphate monohydrate)
Formula: C16H15F6N5O.H3PO4.H2O
Molecular Weight: 523.329
Synonyms: 7-[(3R)-3-Amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine phosphate monohydrate;Sitagliptin phosphate;
EINECS: 682-492-2
Density: N/A
Melting Point: N/A
Boiling Point: 529.9 °C at 760 mmHg
Flash Point: 274.3 °C
Solubility: N/A
Appearance: White or almost white crystalline powder
Hazard Symbols: N/A
Risk Codes: 28-38-41-48-62-63
Safety: 24/25-26-28-36/37/39
Transport Information: N/A
PSA: 173.84000
LogP: 1.66180
Synthetic route
486460-32-6

sitagliptin

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
With phosphoric acid In water; isopropyl alcohol at 70 - 80℃; for 2h; Temperature;97.7%
With phosphoric acid; water In isopropyl alcohol at 20 - 75℃;95%
With phosphoric acid; water In isopropyl alcohol at 75℃;
764667-65-4

1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: isopropyl alcohol; acetic acid / 18 h / 50 °C
2: sodium tetrahydroborate; formic acid / tetrahydrofuran / -30 °C
3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
4: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
Multi-step reaction with 4 steps
1: isopropyl alcohol; acetic acid / 18 h / 50 °C
2: sodium tetrahydroborate; acetic acid / tetrahydrofuran / 3 h / 20 °C
3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
4: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
Multi-step reaction with 3 steps
1.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux
2.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
2.2: 13 h / 50 °C / 10343.2 Torr
3.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
1169707-29-2

(R,Z)-3-[(1-phenylethyl)amino]-1-{3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl}-4-(2,4,5-trifluorophenyl)but-2-en-1-one

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; formic acid / tetrahydrofuran / -30 °C
2: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
3: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; acetic acid / tetrahydrofuran / 3 h / 20 °C
2: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
3: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
1169707-30-5

(3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
2: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
868071-17-4

3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium hydroxide; dicyclohexyl-carbodiimide / tetrahydrofuran; water; cis-1,2-Dichloroethylene / 3 h / 20 - 22 °C
1.2: 18.5 h / 10 - 20 °C
2.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
2.2: 3 h / 0 - 5 °C
3.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
4.1: sodium hydroxide / water / 1 h / 0 - 5 °C
5.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
767352-30-7

N-(benzyloxy)-4(R)-[1-methyl-(2,4,5-trifluorophenyl)]-2-oxoazetidine

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
1.2: 3 h / 0 - 5 °C
2.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
3.1: sodium hydroxide / water / 1 h / 0 - 5 °C
4.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
1361389-75-4

3(R)-3-[(benzyloxy)amino]-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
2: sodium hydroxide / water / 1 h / 0 - 5 °C
3: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme

sitagliptin phosphate

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 0 - 5 °C
2: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
769195-26-8

4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogen; dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) / methanol; acetic acid / 70 °C / 3620.13 Torr / Inert atmosphere; Autoclave
2.1: lithium hydroxide; dicyclohexyl-carbodiimide / tetrahydrofuran; water; cis-1,2-Dichloroethylene / 3 h / 20 - 22 °C
2.2: 18.5 h / 10 - 20 °C
3.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
3.2: 3 h / 0 - 5 °C
4.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
5.1: sodium hydroxide / water / 1 h / 0 - 5 °C
6.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
209995-38-0

(2,4,5-trifluorophenyl)acetic acid

654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: triethylamine; magnesium chloride / acetonitrile / 30 - 50 °C / Inert atmosphere
1.2: 5.5 h / 30 °C / Inert atmosphere
2.1: hydrogen; dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) / methanol; acetic acid / 70 °C / 3620.13 Torr / Inert atmosphere; Autoclave
3.1: lithium hydroxide; dicyclohexyl-carbodiimide / tetrahydrofuran; water; cis-1,2-Dichloroethylene / 3 h / 20 - 22 °C
3.2: 18.5 h / 10 - 20 °C
4.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
4.2: 3 h / 0 - 5 °C
5.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
6.1: sodium hydroxide / water / 1 h / 0 - 5 °C
7.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
Multi-step reaction with 5 steps
1.1: dmap; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 20 - 40 °C
1.2: 2 - 3 h / 0 - 5 °C
2.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C
2.2: 3 - 5 h / 20 - 45 °C
3.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux
4.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
4.2: 13 h / 50 °C / 10343.2 Torr
5.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
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    Sitagliptin monohydrate

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    Name: Sitagliptin monohydrate Synonyms: sitagliptin phosphate monohydrate CAS: 654671-77-9 MF: C16H20F6N5O6P Appearance: White powder Storage:Store in cool and dry place, away from sun light. Package:25KG/Drum Application:Pharmaceutical Raw Materi

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    654671-77-9

    654671-77-9

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    Sitagliptin phosphate monohydrate Basic information Product Name: Sitagliptin phosphate monohydrate Synonyms: 7-[(3R)-3-Amino-1-oxo-4-(2,4,5-trifluorophenyl)Butyl]-5,6,7,8-tetrahydro-3-(

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Chemistry

IUPAC name: (3R)-3-Amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one ; phosphoric acid ; hydrate
Synonyms: 7-((3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4- triazolo(4,3-
a)pyrazine monophosphate monohydrate ; Sitagliptin phosphate hydrate
Molecular Formula: C16H20F6N5O6P
Molecular Weight: 523.32408 g/mol
Flash Point: 274.3 °C
Enthalpy of Vaporization: 80.51 kJ/mol
Boiling Point: 529.9 °C at 760 mmHg
Vapour Pressure: 2.59E-11 mmHg at 25 °C
Following is the Structure of Sitagliptin phosphate monohydrate (CAS NO.654671-77-9):
        

History

 Sitagliptin phosphate monohydrate (CAS NO.654671-77-9) was approved by the U.S. Food and Drug Administration (FDA) on October 17, 2006 and is marketed in the US as Januvia by Merck & Co. On April 2, 2007, the FDA approved an oral combination of sitagliptin and metformin marketed in the US as Janumet.

Uses

1、Sitagliptin phosphate monohydrate  (CAS NO.654671-77-9) works to competitively inhibit the enzyme dipeptidyl peptidase 4 (DPP-4). This enzyme breaks down the incretins GLP-1 and GIP, gastrointestinal hormones that are released in response to a meal.
2、Sitagliptin phosphate monohydrate also has an effect on appetite. By slowing down gastric motility it induces a feeling of satiety. This reduction of appetite can help patients to lose weight, a useful effect in patients with diabetes.

Specification

In clinical trials, adverse effects were as common with sitagliptin (whether used alone or with metformin or pioglitazone) as they were with placebo, except for extremely rare nausea and common cold-like symptoms.There is no significant difference in the occurrence of hypoglycemia between placebo and sitagliptin .

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