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 1811332Notes

Reaction equation

HRID 1811332 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-60464d8bad9143a7b132763e4772a00b
Source dataset
uspto-grants-2013_01
Patent number
US08362251B2

Reaction notes

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