tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

Base Information

• Chemical Name: tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate
• CAS No.: 1620239-42-0
• Molecular Formula: C₃₅H₃₈N₆O₆
• Molecular Weight: 638.723
• Mol file: 1620239-42-0.mol

Synonyms:

Chemical Property of tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

There total 13 articles about tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate 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:

ethyl 3-amino-7-bromoquinoline-2-carboxylate (1260807-99-5) → tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate (1620239-42-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / dichloromethane / -10 - 20 °C

2.1: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium phosphate / 1,4-dioxane / 6 h / 90 °C / Inert atmosphere; Sealed tube

3.1: acetic acid; water / pH 5

4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C

5.1: osmium(VIII) oxide; sodium periodate / water; tetrahydrofuran / 2 h / 70 °C

6.1: tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

6.2: pH 7

7.1: Dess-Martin periodane / dichloromethane / 18 h / 20 °C

With pyridine; potassium phosphate; sodium periodate; osmium(VIII) oxide; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); water; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylate (1620239-11-3) → tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate (1620239-42-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium phosphate / 1,4-dioxane / 6 h / 90 °C / Inert atmosphere; Sealed tube

2.1: acetic acid; water / pH 5

3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C

4.1: osmium(VIII) oxide; sodium periodate / water; tetrahydrofuran / 2 h / 70 °C

5.1: tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

5.2: pH 7

6.1: Dess-Martin periodane / dichloromethane / 18 h / 20 °C

With potassium phosphate; sodium periodate; osmium(VIII) oxide; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); water; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

C22H20N2O4 → tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate (1620239-42-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic acid; water / pH 5

2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C

3.1: osmium(VIII) oxide; sodium periodate / water; tetrahydrofuran / 2 h / 70 °C

4.1: tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

4.2: pH 7

5.1: Dess-Martin periodane / dichloromethane / 18 h / 20 °C

With sodium periodate; osmium(VIII) oxide; water; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

3-amino-7-vinylquinoline-2-carboxylic acid

3-{[(benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acid

benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-vinylquinolin-3-yl)carbamate

benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-formylquinolin-3-yl)carbamate