Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-{4-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-2,2-difluoro-propionamide

HRID 1258720ノート

反応式

HRID 1258720 の反応式
[F:1][C:2]([F:7])([CH3:6])[C:3](O)=[O:4].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][C:34]=1[NH:41][C:42]1[N:46]([CH3:47])[C:45]2[CH:48]=[C:49]([N:53]3[CH2:58][CH2:57][CH:56]([C:59]([F:62])([F:61])[F:60])[CH2:55][CH2:54]3)[C:50]([Cl:52])=[CH:51][C:44]=2[N:43]=1>CN(C=O)C.[Cl-].[Na+].O>[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH:38][C:3](=[O:4])[C:2]([F:7])([F:1])[CH3:6])=[CH:35][C:34]=1[NH:41][C:42]1[N:46]([CH3:47])[C:45]2[CH:48]=[C:49]([N:53]3[CH2:54][CH2:55][CH:56]([C:59]([F:61])([F:60])[F:62])[CH2:57][CH2:58]3)[C:50]([Cl:52])=[CH:51][C:44]=2[N:43]=1

参加物

6

反応物 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27828252,2-Difluoropropionic acidHCID 679580774-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine

生成物 1

HCID 86674341N-{4-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-2,2-difluoro-propionamide

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-difluoropropanoic acid (37 mg; 0.34 mmol), HBTU (129 mg; 0.34 mmol) and TEA (69 mg; 0.68 mmol) in DMF (1.5 mL) was stirred for 30 min at rt and added to a solution of 4-chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine (161 mg; 0.34 mmol) in DMF (1.5 mL). The resulting mixture was stirred overnight at rt, poured into brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated and the residue was purified by column chromatography.

後処理

  1. stirringThe resulting mixture was stirred overnight at rt
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was 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-60be103dc9ae4d64a5db50376d761147
出典データセット
uspto-grants-2013_06
特許番号
US08466186B2

反応ノート

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