N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-formamide → N-{3-[3-methyl-4-oxo-5-(2-pyrrolidin-1-yl-ethyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-formamide

HRID 905819Notes

Reaction equation

HRID 905819 reaction equation
[CH3:1][C:2]1[C:6]2[C:7](=[O:18])[N:8]([CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9][CH2:10][C:5]=2[NH:4][C:3]=1[CH:19]=O.[O:21]=[C:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH:31][CH:32]=[O:33])[CH:28]=2)[NH:23]1>>[CH3:1][C:2]1[C:6]2[C:7](=[O:18])[N:8]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:9][CH2:10][C:5]=2[NH:4][C:3]=1[CH:19]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH:31][CH:32]=[O:33])[CH:28]=2)[NH:23][C:22]1=[O:21]

Participants

3

Reactant 2

HCID 23439025N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-formamideHCID 866376753-methyl-4-oxo-5-(2-pyrrolidin-1-yl-ethyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

Product 1

HCID 86637685N-{3-[3-methyl-4-oxo-5-(2-pyrrolidin-1-yl-ethyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-formamideYield 87.9%

Procedure

The title compound was prepared under the same conditions as described in Example 13 with 3-methyl-4-oxo-5-(2-pyrrolidin-1-yl-ethyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde and N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-formamide as starting materials to give N-{3-[3-methyl-4-oxo-5-(2-pyrrolidin-1-yl-ethyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-formamide (48 mg, 87.9%) as an orange solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-7f8719f02ab94196835dbcdeb7601a68
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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