Malic Acid → 5-(2-Diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one malate

HRID 905888Notes

Reaction equation

[CH2:1]([N:3]([CH2:36][CH3:37])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=4[F:33])[NH:19][C:18]3=[O:34])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:35])[CH3:2].[OH:38][CH:39]([CH2:43][C:44]([OH:46])=[O:45])[C:40]([OH:42])=[O:41]>>[C:40]([OH:42])(=[O:41])[CH:39]([CH2:43][C:44]([OH:46])=[O:45])[OH:38].[CH2:36]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=4[F:33])[NH:19][C:18]3=[O:34])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:35])[CH3:37]

Participants

Reactant 2

HCID 525Malic Acid

HCID 666066855-(2-Diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 666077155-(2-Diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one malate

Procedure

The title compound was prepared under the same conditions described in Example 132 with 5-(2-diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one prepared from Example 39 and 2-hydroxyl-succinic acid as starting materials to give 2-(5-fluoro-2-oxo-1,2-dihydro-5-(2-diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one malate (15 g, 94%) as a yellow solid.

Sources & evidence

ORD record: ord-764ff278f15949cb946f7a991dee6dbf
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012966B2

Reaction notes

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