Methanesulfonic anhydride → 6-(2-Methanesulfonylamino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-Phenyl)-amide

HRID 1094505노트

반응식

HRID 1094505 반응식
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][C:31]4[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[N:32]=4)=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:13][C:12]=1[C:38]([F:41])([F:40])[F:39]>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][C:31]4[CH:36]=[CH:35][N:34]=[C:33]([NH:37][S:2]([CH3:1])(=[O:5])=[O:3])[N:32]=4)=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:13][C:12]=1[C:38]([F:40])([F:39])[F:41]

참가 물질

7

반응물 2

HCID 81560Methanesulfonic anhydrideHCID 160715501-Naphthalenecarboxamide, 6-[(2-amino-4-pyrimidinyl)oxy]-N-[4-fluoro-3-(trifluoromethyl)phenyl]-

생성물 1

HCID 236528646-(2-Methanesulfonylamino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-Phenyl)-amide

시약·촉매·용매 4

HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

378 mg (2.17 mMol) methansulfonic acid anhydride are added in 3 portions to a solution of 300 mg (0.68 mMol) 6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (Step 10.3) in 4.5 ml CH2Cl2 and 7.5 ml pyridine. After 20 h, the solution is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2/THF 50:1-9:1) gives the title compound: m.p.: 246° C.; MS: [M−1]=519.

후처리

  1. customthe aq. phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ae4692db7e8b4ddda29b2f5fcb60a318
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133886B2

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