Dimethylalumanylium chloride → 4-{5-[5-Chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl}-benzonitrile

HRID 2204328Notes

Reaction equation

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

Participants

Reactant 2

HCID 16686359Dimethylalumanylium chloride

HCID 867031372-[[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-ylamino]-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 867031364-{5-[5-Chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl}-benzonitrile

Procedure

The title compound was prepared in analogy to the procedure described for Step F1, but 2-[[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-ylamino]-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step AF2) was used instead of 2-[(4-chloro-phenyl)-(4-hydroxy-cyclohexylamino)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester, and dimethylaluminium chloride [1184-58-3] (1M/hexanes) was used instead of trimethylaluminium. The title compound was obtained as a white solid. ESI-MS: tR=1.00 min, [M+H]+ 513/515 (LC-MS 1).

Workup

customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record: ord-34274ef123ee41d4b94246ff578ea5c2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365576B2

Reaction notes

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