3-Chloro-4-fluoroaniline → 2-Bromo-5-[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204317Notes

Reaction equation

HRID 2204317 reaction equation
C(OC(C1C=CN(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O)C.[NH2:23][C:24]1[CH:25]=[C:26]([Cl:40])[C:27](=[O:39])[N:28]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[CH:29]=1.C[O:42][C:43]([C:45]1[CH:49]=[C:48]([Br:50])[N:47]([CH:51]([CH3:53])[CH3:52])[C:46]=1[CH:54]([C:56]1[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][CH:57]=1)O)=O.ClC1C=C(C=CC=1F)N>>[Br:50][C:48]1[N:47]([CH:51]([CH3:52])[CH3:53])[C:46]2[CH:54]([C:56]3[CH:57]=[CH:58][C:59]([Cl:62])=[CH:60][CH:61]=3)[N:23]([C:24]3[CH:25]=[C:26]([Cl:40])[C:27](=[O:39])[N:28]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=4)[CH:29]=3)[C:43](=[O:42])[C:45]=2[CH:49]=1

Participants

5

Reactant 4

HCID 97083-Chloro-4-fluoroanilineHCID 867031015-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 867031052-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 867031245-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one

Product 1

HCID 867031232-Bromo-5-[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Procedure

The title compound was prepared in analogy to the procedure described for Step D2, but 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step E4) and 5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one (Step O4) were used instead of 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester and 3-chloro-4-fluoroaniline respectively to afford the title compound as a green-blue foam. tR: 5.47 min (HPLC 1); ESI-MS: tR=1.33 min, [M+H]+ 568/570/572 (LC-MS 1); TLC: Rf=0.30 (1:1 EtOAc/heptanes).

Workup

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

Sources & evidence

ORD record
ord-c99e317e2cba4a9091afce2f133fd4c2
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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