Triethylamine → 6-Methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

HRID 556354노트

반응식

HRID 556354 반응식
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7]([C:10]([OH:12])=O)=[N:8][S:9][C:5]=2[CH:4]=1.[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24].CCN(CC)CC.CCCP(=O)=O>CN(C=O)C.CCOC(C)=O.O>[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:10]([C:7]2[C:6]3[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[S:9][N:8]=2)=[O:12])=[CH:18][C:17]=1[C:23]([F:24])([F:25])[F:26]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 16167369Propylphosphoric anhydride2회HCID 666368056-Methoxybenzo[d]isothiazole-3-carboxylic acid

생성물 1

HCID 669929426-Methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

209 mg (1.00 mMol) 6-methoxy-benzo[d]isothiazole-3-carboxylic acid (preparation see: WO 2004/029050, Procedure N), 269 mg (1.5 mMol) 4-fluoro-3-trifluoromethyl-aniline and 1.4 ml (10 mMol) Et3N are dissolved in 5 ml of dry DMF and cooled in an ice-bath. Then a solution of 1.17 ml (50% in DMF; 2.0 mMol) propylphosphonic anhydride is added. The mixture is stirred for 15 h at rt, when another 0.58 ml of propylphosphonic anhydride are added. After 2 h, the reaction mixture is poured into water and EtOAc, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and partially concentrated. Addition of hexane precipitates the title compound: m.p.: 157° C.; MS: [M+1]+=371.

후처리

  1. temperaturecooled in an ice-bath
  2. waitAfter 2 h
  3. customthe aq. phase separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed twice with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationpartially concentrated
  8. additionAddition of hexane
  9. customprecipitates the title compound

출처 및 근거

ORD 기록
ord-c747789c82d94f079eb4aaf867528a28
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058276B2

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