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

HRID 2204345Notes

Reaction equation

HRID 2204345 reaction equation
O=[O+][O-].CO[C:6]([C:8]1[CH:12]=[C:11]([Br:13])[N:10]([CH:14]([CH3:16])[CH3:15])[C:9]=1[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)O)=[O:7].[CH3:26][N:27]1[CH:31]=[C:30]([NH2:32])[C:29]([CH3:33])=[N:28]1.C(OC(C1C=CN(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O)C.NC1C=C(Cl)C(=O)N(CC2C=CC(OC)=CC=2)C=1.O(S(C)(=O)=O)S(C)(=O)=O>CCN(CC)CC>[Br:13][C:11]1[N:10]([CH:14]([CH3:16])[CH3:15])[C:9]2[CH:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[N:32]([C:30]3[C:29]([CH3:33])=[N:28][N:27]([CH3:26])[CH:31]=3)[C:6](=[O:7])[C:8]=2[CH:12]=1

Participants

8

Reactant 6

HCID 24823OzoneHCID 81560Methanesulfonic anhydrideHCID 44310561,3-dimethyl-1H-pyrazol-4-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 867031245-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one

Product 1

HCID 867031482-Bromo-6-(4-chloro-phenyl)-5-(1,3-dimethyl-1H-pyrazol-4-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 O1 but in the step corresponding to Step O3, 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step D3) and 1,3-dimethyl-1H-pyrazol-4-ylamine (free base generated from the hydrochloride salt [1147222-02-3]) were used instead of 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester and 5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one respectively. Moreover, in this step, the procedure described for Step L3 using Ms2O and Et3N was used. The title compound was obtained as a beige solid. tR: 1.18 min (HPLC 3); ESI-MS: tR=1.22 min, [M+H]+ 415/417 (LC-MS 1); TLC: Rf=0.24 (2:1 EtOAc/hexanes).

Workup

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

Sources & evidence

ORD record
ord-c54f1edee82641d79aeadab73fd76302
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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