3-Chloro-4-fluoroaniline → 2-Bromo-6-(4-chloro-2-fluoro-phenyl)-5-(2,5-dimethyl-2H-pyrazol-3-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204351Notes

Reaction equation

HRID 2204351 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([CH3:8])=[N:3]1.C[O:10][C:11]([C:13]1[CH:17]=[C:16]([Br:18])[N:15]([CH:19]([CH3:21])[CH3:20])[C:14]=1[CH:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[F:31])O)=O.ClC1C=C(C=CC=1F)N.COC(C1C=C(Br)N(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O.O(S(C)(=O)=O)S(C)(=O)=O>CCN(CC)CC>[Br:18][C:16]1[N:15]([CH:19]([CH3:21])[CH3:20])[C:14]2[CH:22]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[F:31])[N:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:8])[CH:5]=3)[C:11](=[O:10])[C:13]=2[CH:17]=1

Participants

7

Reactant 5

HCID 97083-Chloro-4-fluoroanilineHCID 81560Methanesulfonic anhydrideHCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 867031015-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 867031585-bromo-2-[(4-chloro-2-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867031572-Bromo-6-(4-chloro-2-fluoro-phenyl)-5-(2,5-dimethyl-2H-pyrazol-3-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound was prepared in analogy to the procedure described for Intermediate D but in the step corresponding to Step D2, 2,5-dimethyl-2H-pyrazol-3-ylamine [3524-32-1] and 5-bromo-2-[(4-chloro-2-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step BI1) were used instead of 3-chloro-4-fluoroaniline and 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester respectively. Moreover, in this step, the procedure described for Step L3 using Ms2O and Et3N was used. The title compound (containing some of the corresponding 2-chloro analog) was obtained as a solid. ESI-MS: tR=1.14 min, [M+H]+ 465/467/469 (LC-MS 1).

Workup

  1. customThe title compound was prepared in analogy to the procedure
  2. customwas obtained as a solid

Sources & evidence

ORD record
ord-8455e3d55da34de0a0633a68dfb4c05d
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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