trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine

Base Information

• Chemical Name: trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine
• CAS No.: 1416224-52-6
• Molecular Formula: C₁₈H₂₃N₃O₂
• Molecular Weight: 313.4
• Mol file: 1416224-52-6.mol

Synonyms:trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine

Chemical Property of trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine

There total 13 articles about trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

[trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (1416224-51-5) → trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine (1416224-52-6)

Guidance literature:

[trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 0 - 25 ℃; for 2h;

With sodium hydroxide; In dichloromethane; water; pH=12;

Reference yield:

8-bromo-7-chloro-2-methoxy-1,5-naphthyridine (915976-85-1) → trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine (1416224-52-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: N,N-dimethyl-formamide / 8 h / 130 °C

2.1: sodium hydride / tetrahydrofuran / 2 h / -30 °C

3.1: sodium hydroxide; dihydrogen peroxide / manganese(IV) oxide / water; methanol / 1 h / 70 °C

4.1: Schwartz's reagent / tetrahydrofuran / 0.17 h / 18 - 25 °C

5.1: phosphorus tribromide / dichloromethane / 1 h / 18 - 25 °C

5.2: pH 7

6.1: toluene / 6 h / Reflux

7.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C

7.2: 15 h / 18 - 25 °C

8.1: 4-methylmorpholine N-oxide / potassium osmate(VI) dihydrate / water; acetone / 15 h / 18 - 25 °C

9.1: toluene / 2 h / 70 °C

10.1: triethylamine; hydrogen / palladium-on-charcoal / methanol / 1 h / 18 - 25 °C / 750.08 Torr

11.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 25 °C

12.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 25 °C

12.2: pH 12

With Schwartz's reagent; hydrogen; dihydrogen peroxide; phosphorus tribromide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; diethylazodicarboxylate; manganese(IV) oxide; potassium osmate(VI) dihydrate; palladium-on-charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 11.1: Mitsunobu reaction;

Reference yield:

3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carbonitrile (1312577-92-6) → trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine (1416224-52-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydroxide; dihydrogen peroxide / manganese(IV) oxide / water; methanol / 1 h / 70 °C

2.1: Schwartz's reagent / tetrahydrofuran / 0.17 h / 18 - 25 °C

3.1: phosphorus tribromide / dichloromethane / 1 h / 18 - 25 °C

3.2: pH 7

4.1: toluene / 6 h / Reflux

5.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C

5.2: 15 h / 18 - 25 °C

6.1: 4-methylmorpholine N-oxide / potassium osmate(VI) dihydrate / water; acetone / 15 h / 18 - 25 °C

7.1: toluene / 2 h / 70 °C

8.1: triethylamine; hydrogen / palladium-on-charcoal / methanol / 1 h / 18 - 25 °C / 750.08 Torr

9.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 25 °C

10.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 25 °C

10.2: pH 12

With Schwartz's reagent; hydrogen; dihydrogen peroxide; phosphorus tribromide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; diethylazodicarboxylate; manganese(IV) oxide; potassium osmate(VI) dihydrate; palladium-on-charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 9.1: Mitsunobu reaction;

upstream raw materials:

8-bromo-7-chloro-2-methoxy-1,5-naphthyridine

3-chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile

3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carbonitrile

3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

Downstream raw materials:

3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-amide