N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxyacetamide → HCID 25114923, compound

HRID 2191449Notes

Reaction equation

HRID 2191449 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][C:31](=[O:34])[CH2:32][OH:33])[NH:26][C:25](=[O:35])[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:35])[NH:26][C:27]4[C:23]\3=[CH:22][C:21]([F:20])=[C:29]([NH:30][C:31](=[O:34])[CH2:32][OH:33])[CH:28]=4)=[C:14]([CH3:15])[C:7]=2[C:6]1=[O:18]

Participants

3

Reactant 2

HCID 45118149N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxyacetamideHCID 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 25114923HCID 25114923, compoundYield 83.4%

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 N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-acetamide 27b as starting materials to obtain (Z)—N-{3-[5-(2-dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepin-2-ylmethylene]-5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl}-2-hydroxy-acetamide 27 (80 mg, yield 83.4%) as an orange solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-026950ace1f843a3a4ad1620bbf4eefa
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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