5-(2-diethylaminoethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde → N-{3-[5-(2-diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-ylmethylene]-5-fluoro dihydro-1H-indol-7-yl}-acetamide

HRID 2364987Notes

Reaction equation

HRID 2364987 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=O)=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:18])[CH3:2].[F:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([NH:31][C:32](=[O:34])[CH3:33])[CH:30]=1)[NH:27][C:26](=[O:35])[CH2:25]2.NC1C=C(F)C=C2C=1NC(=O)C2>>[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:25]3[C:24]4[C:28](=[C:29]([NH:31][C:32](=[O:34])[CH3:33])[CH:30]=[C:22]([F:21])[CH:23]=4)[NH:27][C:26]3=[O:35])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:18])[CH3:2].[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:25]3[CH:24]4[C:28](=[C:29]([NH:31][C:32](=[O:34])[CH3:33])[CH:30]=[C:22]([F:21])[CH2:23]4)[NH:27][CH2:26]3)=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 250230155-(2-diethylaminoethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehydeHCID 592500547-Amino-5-fluoroindolin-2-oneHCID 66608895N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-acetamide

Product 2

HCID 66607959N-{3-[5-(2-diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-ylmethylene]-5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl}-acetamideHCID 66608227N-{3-[5-(2-diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-ylmethylene]-5-fluoro dihydro-1H-indol-7-yl}-acetamideYield 30.8%

Procedure

The title compound was prepared under the same conditions as described in Example 1 with 5-(2-diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde and N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-acetamide which was prepared by the acetylation of 7-amino-5-fluoro-1,3-dihydro-indole-2-one (prepared according to U.S. Pat. No. 6,114,371, US1997-810659) as starting materials to give N-{3-[5-(2-diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-ylmethylene]-5-fluoro dihydro-1H-indol-7-yl}-acetamide (36 mg, 30.8%) as a yellow solid.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-84468c59cd1f4dcda18c54e2bb3374e3
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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