Dichloromethane → 2-(6-(4-fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidine-1-carboxamide

HRID 13285

반응식

HRID 13285 반응식
CN(C1C=CC=CN=1)C.C[Si]([N:14]=[C:15]=[O:16])(C)C.C(Cl)Cl.[F:20][C:21]1[CH:47]=[CH:46][C:24]([O:25][C:26]2[C:40]([CH:41]3[CH2:45][CH2:44][CH2:43][NH:42]3)=[CH:39][C:29]3[NH:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:32][C:28]=3[CH:27]=2)=[CH:23][CH:22]=1>O>[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:25][C:26]2[C:40]([CH:41]3[CH2:45][CH2:44][CH2:43][N:42]3[C:15]([NH2:14])=[O:16])=[CH:39][C:29]3[NH:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:32][C:28]=3[CH:27]=2)=[CH:46][CH:47]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 218852-DimethylaminopyridineHCID 70696Trimethylsilyl isocyanateHCID 231455755-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

생성물 1

HCID 231453492-(6-(4-fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidine-1-carboxamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2 mg of dimethylaminopyridine and 0.059 ml of trimethylsilyl isocyanate were added in order to a methylene chloride (1 ml) solution of 31.2 mg of 5-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole obtained in Example 168, and the reaction liquid was stirred overnight at room temperature. Water was added to the reaction liquid, and extracted with ethyl acetate, and then washed with saturated saline. After dried and concentrated, the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid] to obtain the entitled compound as a white solid.

후처리

  1. customthe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated saline
  4. customAfter dried
  5. concentrationconcentrated
  6. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]

출처 및 근거

ORD 기록
ord-451f1694396b4bcab57ee743ed2e574c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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