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 1258720노트

반응식

HRID 1258720 반응식
[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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60be103dc9ae4d64a5db50376d761147
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466186B2

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