Hydrochloric Acid → Methyl 2-[3-({[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}amino)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616171Notes

Reaction equation

HRID 1616171 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:12]=2)[C:7]1=[O:20].Cl.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35]([CH3:41])([C:38](O)=[O:39])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35]([C:38]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[CH2:5][N:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][C:10]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:12]=3)[C:7]2=[O:20])=[O:39])([CH3:41])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 67282939Methyl 2-(3-aminobenzyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67282976Methyl 2-[3-({[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}amino)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-(3-aminobenzyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate.HCl (0.22 g, 0.64 mmol) in pyridine (5 mL) was added 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.17 g, 0.70 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.37 g, 1.9 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was then concentrated and the crude residue was purified by flash silica gel chromatography (0% to 5% EtOAc/DCM) to afford methyl 2-[3-({[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}amino)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.29 g, 83%). LC-MS: (FA) ES+ 434.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe crude residue was purified by flash silica gel chromatography (0% to 5% EtOAc/DCM)

Sources & evidence

ORD record
ord-3b1892c04f344e24a0ba4a813e6cc34b
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

Loading…