4-Bromoaniline → N-(4-Bromo-phenyl)-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1410245ノート

反応式

HRID 1410245 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([O:31][CH2:32][CH:33]([F:35])[F:34])[C:26]([C:28](O)=[O:29])=[CH:27][C:20]=2[N:19]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:60][C:61]1[CH:67]=[CH:66][C:64]([NH2:65])=[CH:63][CH:62]=1>CN(C=O)C.[Cl-].[Na+].O>[Br:60][C:61]1[CH:67]=[CH:66][C:64]([NH:65][C:28]([C:26]2[C:25]([O:31][CH2:32][CH:33]([F:34])[F:35])=[CH:24][C:21]3[N:22]([CH3:23])[C:18]([NH:17][C:3]4[CH:4]=[C:5]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH:6]=[CH:7][C:2]=4[Cl:1])=[N:19][C:20]=3[CH:27]=2)=[O:29])=[CH:63][CH:62]=1

参加物

6

反応物 3

HCID 78074-BromoanilineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866463402-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid

生成物 1

HCID 86646339N-(4-Bromo-phenyl)-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of 2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid (1.12 g; 2.19 mmol), HBTU (831 mg; 2.19 mmol) and TEA (433 mg; 4.38 mmol) in DMF (10 mL) was stirred for 30 min at rt and thereafter added to a solution of 4-bromoaniline (377 mg; 2.19 mmol) in DMF (10 mL). The resulting mixture was stirred over night at rt, poured into brine and extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give the sub-title compound. Yield: 1.35 g (93%).

後処理

  1. stirringThe resulting mixture was stirred over night at rt
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-30c7fdd20980419ba1ceb34e236d8cad
出典データセット
uspto-grants-2014_12
特許番号
US08921405B2

反応ノート

読み込み中…