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

HRID 2204356Notes

Reaction equation

HRID 2204356 reaction equation
CO[C:3]([C:5]1[CH:9]=[C:8]([Br:10])[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]=1[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)O)=[O:4].[NH2:23][C:24]1[C:25](=[O:40])[N:26]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[CH:27]=[C:28]([Cl:30])[CH:29]=1.COC(C1C=C(Br)N(C(C)C)C=1C(C1C=CC(C#N)=CC=1)O)=O.CN1C(N)=CC(C)=N1>>[Br:10][C:8]1[N:7]([CH:11]([CH3:12])[CH3:13])[C:6]2[CH:14]([C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[N:23]([C:24]3[C:25](=[O:40])[N:26]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[CH:27]=[C:28]([Cl:30])[CH:29]=3)[C:3](=[O:4])[C:5]=2[CH:9]=1

Participants

5

Reactant 4

HCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 867031015-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 867031523-amino-5-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-oneHCID 867031555-bromo-2-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867031652-Bromo-5-[5-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-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 Intermediate AX but in the step corresponding to Step AX1, 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (step D3) and 3-amino-5-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one (Step AH1) were used instead of 5-bromo-2-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester and 2,5-dimethyl-2H-pyrazol-3-ylamine respectively. The title compound was obtained as a white solid. tR: 1.38 min (HPLC 3); ESI-MS: tR=1.35 min, [M+H]+ 600/602/604 (LC-MS 1); TLC: Rf=0.46 (1:1 EtOAc/heptanes).

Workup

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

Sources & evidence

ORD record
ord-325b5f9b3e254af4b1b53c3fa13fbb59
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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