Dichloromethane → 5-(2-Ethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 2365136Notes

Reaction equation

HRID 2365136 reaction equation
C[N:2]([CH3:30])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[NH:11][C:12]([CH:15]=[C:16]3[C:24]4[C:19](=[CH:20]C=C(NC=O)[CH:23]=4)[NH:18][C:17]3=[O:28])=[C:13]([CH3:14])[C:7]=2[C:6]1=[O:29].F[C:32]([F:37])(F)[C:33](O)=O.Cl[CH2:39]Cl>>[CH2:30]([NH:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[NH:11][C:12]([CH:15]=[C:16]3[C:24]4[C:19](=[CH:20][CH:33]=[C:32]([F:37])[CH:23]=4)[NH:18][C:17]3=[O:28])=[C:13]([CH3:14])[C:7]=2[C:6]1=[O:29])[CH3:39]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 72526798N-{3-[5-(2-dimethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-formamide

Product 1

HCID 666075355-(2-Ethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 98%

Procedure

A stirred solution of ethyl-{2-[2-(6-fluoro-2-oxo-indan-1-ylidenemethyl)-3-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-5-yl]-ethyl}-carbamic acid tert-butyl ester (1.2 g, 2.5 mmol) obtained from Example 116 in dichloromethane (25 ml) was added dropwise slowly With 2.5 ml of trifluoroacetic acid. Upon the completion of the addition, the mixture was stirred for 2 hours at room temperature. The mixture was concentrated under reduced pressure to give 5-(2-ethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (0.94 g, 98%) as a yellow solid.

Workup

  1. additionUpon the completion of the addition
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f52551cedb824a2cb4cc0ccf1051a297
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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