Isobutyl chloroformate → {4-[5-(4-Fluoro-3-trifluoromethyl-phenylcarbamoyl)-naphthalen-2-yloxy]-pyrimidin-2-yl}carbamic acid isobutyl ester

HRID 1094503ノート

反応式

HRID 1094503 の反応式
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[F:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:29][C:30]4[CH:35]=[CH:34][N:33]=[C:32]([NH2:36])[N:31]=4)=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:12][C:11]=1[C:37]([F:40])([F:39])[F:38]>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O.O>[CH2:5]([O:4][C:2](=[O:3])[NH:36][C:32]1[N:31]=[C:30]([O:29][C:25]2[CH:26]=[CH:27][C:28]3[C:23](=[CH:22][CH:21]=[CH:20][C:19]=3[C:17](=[O:18])[NH:16][C:13]3[CH:14]=[CH:15][C:10]([F:9])=[C:11]([C:37]([F:40])([F:39])[F:38])[CH:12]=3)[CH:24]=2)[CH:35]=[CH:34][N:33]=1)[CH:6]([CH3:8])[CH3:7]

参加物

7

反応物 2

HCID 62365Isobutyl chloroformateHCID 160715501-Naphthalenecarboxamide, 6-[(2-amino-4-pyrimidinyl)oxy]-N-[4-fluoro-3-(trifluoromethyl)phenyl]-

生成物 1

HCID 23652795{4-[5-(4-Fluoro-3-trifluoromethyl-phenylcarbamoyl)-naphthalen-2-yloxy]-pyrimidin-2-yl}carbamic acid isobutyl ester

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

110 μl (0.84 mMol) isobutyl chloroformate are added portionwise 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 1 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-CH2Cl2/EtOH 19:1) gives the title compound: MS: [M+1]+=543.

後処理

  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

出典と根拠

ORDレコード
ord-3f2524e1b6d84e93a9a3fb39d57362f6
出典データセット
uspto-grants-2012_03
特許番号
US08133886B2

反応ノート

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