5-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester → 5-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid

HRID 2204311Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:10]=[C:9]([Br:11])[N:8]([CH2:12][CH3:13])[C:7]=1[CH:14]([NH:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[CH3:30])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:5])C.COC(C1C=C(Br)N(C(C)C)C=1C(NC1C=CC(F)=C(Cl)C=1)C1C=CC(Cl)=CC=1)=O>>[Br:11][C:9]1[N:8]([CH2:12][CH3:13])[C:7]([CH:14]([NH:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=2[CH3:30])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1

Participants

Reactant 2

HCID 867031005-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

HCID 867031165-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 867031155-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid

Procedure

The title compound was prepared in analogy to the procedure described for Step D1 but 5-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step K2) was used instead of was used instead of 5-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester to afford the title compound as a colorless oil. tR: 5.97 min (HPLC 4); ESI-MS: tR=1.41 min, [M−H] 479/481/483 (LC-MS 1).

Workup

customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record: ord-1125f1bde8764a399eaac1b0ff422e53
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365576B2

Reaction notes

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