Ethyl orthoformate → 1-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline

HRID 1108626Notes

Reaction equation

HRID 1108626 reaction equation
[CH:1](OCC)(OCC)OCC.[NH2:11][C:12]1[C:13]([Cl:37])=[N:14][C:15]2[C:20]([C:21]=1[NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[CH:19][CH:18]=[CH:17][CH:16]=2>>[CH2:30]([O:29][C:27]([NH:26][CH2:25][CH2:24][CH2:23][N:22]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([Cl:37])[C:12]=2[N:11]=[CH:1]1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 187839713-Amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline

Product 1

HCID 187839491-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline

Conditions

Temperature
100 °C

Procedure

0.52 ml (3.12 mmol) of triethyl ortho-formate was added to 0.12 g (0.312 mmol) of of 3-amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline. The mixture was heated at 100° C. and stirred for 3.5 hours. The reaction mixture was concentrated under reduced pressure to obtain 0.12 g (0.304 mmol) of 1-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]-quinoline (shown below) as a pale yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-066317361f624f66bda1acebc5efb10d
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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