Diethyl aluminum chloride → 4-[5-(5-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl]-2-fluoro-benzonitrile

HRID 2204404Notes

Reaction equation

HRID 2204404 reaction equation
[Cl-].C([Al+]CC)C.CO[C:9]([C:11]1[CH:15]=[C:14]([C:16]2[C:17]([O:24][CH3:25])=[N:18][C:19]([O:22][CH3:23])=[N:20][CH:21]=2)[N:13]([CH:26]([CH3:28])[CH3:27])[C:12]=1[CH:29]([NH:39][C:40]1[CH:45]=[C:44]([Cl:46])[C:43](=[O:47])[N:42]([CH3:48])[CH:41]=1)[C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[C:32]([F:38])[CH:31]=1)=[O:10]>>[Cl:46][C:44]1[C:43](=[O:47])[N:42]([CH3:48])[CH:41]=[C:40]([N:39]2[C:9](=[O:10])[C:11]3[CH:15]=[C:14]([C:16]4[C:17]([O:24][CH3:25])=[N:18][C:19]([O:22][CH3:23])=[N:20][CH:21]=4)[N:13]([CH:26]([CH3:27])[CH3:28])[C:12]=3[CH:29]2[C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[C:32]([F:38])[CH:31]=2)[CH:45]=1

Participants

3

Reactant 2

HCID 16686102Diethyl aluminum chlorideHCID 867032172-[(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-ylamino)-(4-cyano-3-fluoro-phenyl)-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867032164-[5-(5-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl]-2-fluoro-benzonitrile

Procedure

The title compound was prepared in analogy to the procedure described for Step H1 but diethylaluminium chloride (1.8M in toluene) [96-10-6] was used instead of trimethylaluminium chloride, and 2-[(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-ylamino)-(4-cyano-3-fluoro-phenyl)-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step 195.1) was used instead of 2-[(3-chloro-4-fluoro-phenylamino)-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester. The title compound was obtained as a white solid. tR: 1.07 min (HPLC 3); ESI-MS: tR=0.93 min, [M+H]+ 563/565 (LC-MS 1); TLC: Rf=0.06 (EtOAc).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-90e4aa63735f4c83a7ff36483a3574fa
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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