5-Fluoro-6-(4-fluoro-benzylamino)-1,3-dihydro-indol-2-one → HCID 25115604, compound

HRID 2191473Notes

Reaction equation

HRID 2191473 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][C:8]2[NH:12][C:13]([CH:16]=O)=[C:14]([CH3:15])[C:7]=2[C:6]1=[O:18].[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][C:29]=1[NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[NH:26][C:25](=[O:39])[CH2:24]2>>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][C:8]2[NH:12][C:13](/[CH:16]=[C:24]3\[C:25](=[O:39])[NH:26][C:27]4[C:23]\3=[CH:22][C:21]([F:20])=[C:29]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH:28]=4)=[C:14]([CH3:15])[C:7]=2[C:6]1=[O:18]

Participants

3

Reactant 2

HCID 592500565-Fluoro-6-(4-fluoro-benzylamino)-1,3-dihydro-indol-2-oneHCID 592500735-(2-Dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 25115604HCID 25115604, compoundYield 43.7%

Procedure

The title compound was prepared under the same conditions as described in step 4 of Example 23 with 5-(2-dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 23c obtained from step 3 of Example 23 and 5-fluoro-6-(4-fluoro-benzylamino)-1,3-dihydro-indol-2-one 3e obtained from step 4 of Example 3 were used as starting materials to obtain (Z)-5-(2-dimethylamino-ethyl)-2-[5-fluoro-6-(4-fluoro-benzylamino)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-c]azepin-4-one 43 (50 mg, yield 43.7%) as a red solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-519de3399fec439b8835cc69afca4c54
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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