1,3-Dimethyl-1H-pyrazol-5-amine → 5-bromo-2-[(4-chloro-phenyl)-(2,5-dimethyl-2H-pyrazol-3-ylamino)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

HRID 2204343Notes

Reaction equation

HRID 2204343 reaction equation
[CH3:1][O:2][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].[CH3:23][N:24]1[C:28]([NH2:29])=[CH:27][C:26]([CH3:30])=[N:25]1.C(OC(C1C=CN(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O)C.NC1C(=O)N(C)C=C(Cl)C=1>>[CH3:1][O:2][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)[NH:29][C:28]1[N:24]([CH3:23])[N:25]=[C:26]([CH3:30])[CH:27]=1)=[O:4]

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 867031052-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 867031183-Amino-5-chloro-1-methylpyridin-2(1H)-one

Product 1

HCID 867031455-bromo-2-[(4-chloro-phenyl)-(2,5-dimethyl-2H-pyrazol-3-ylamino)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Procedure

The title compound was prepared in analogy to the procedure described for Step L3 but 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (step D3) and 2,5-dimethyl-2H-pyrazol-3-ylamine [3524-32-1] were used instead of 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester and 3-amino-5-chloro-1-methyl-1H-pyridin-2-one respectively. The title compound was obtained as a foam. ESI-MS: tR=1.29 min, [M+H]+ 479/481/483 (LC-MS 1); TLC: Rf=0.31 (1:1 CH2Cl2/EtOAc).

Workup

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

Sources & evidence

ORD record
ord-42b82508a0224d8bb6e67c3f3242fe8f
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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