Pyrrolidine → 2-(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-1-pyrrolidin-1-yl-ethanone

HRID 2067208Notes

Reaction equation

HRID 2067208 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])[CH:25]=[CH:24][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[N:14]=[N:15][N:16]([CH2:18][C:19]([NH:21][CH2:22][CH3:23])=[O:20])[CH:17]=2)[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5].Cl[C:38]1C=C(NC2C=CC(F)=CC=2F)C=C[C:39]=1C(C1C=C(C2N=NN(CC(O)=O)C=2)C=CC=1C)=O.N1CCCC1>>[Cl:1][C:2]1[CH:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])[CH:25]=[CH:24][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[N:14]=[N:15][N:16]([CH2:18][C:19]([N:21]3[CH2:39][CH2:38][CH2:23][CH2:22]3)=[O:20])[CH:17]=2)[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5]

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 11496723(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-acetic acidHCID 115986752-(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-N-ethyl-acetamide

Product 1

HCID 116782192-(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-1-pyrrolidin-1-yl-ethanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 112, using compound 111 (0.12 mmol) and pyrolidine (0.12 mmol). The crude product was purified by continuous gradient flash chromatography using MeOH/EtOAc 0:100 to 5:95 as the eluent to afford the title compound as almost yellow syrup.

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-518ba65f15d6465db1cc9430d9758e91
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

Loading…