Acetic Anhydride → N-{2-[6-(2-Acetylamino-benzothiazol-4-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenyl}-acetamide

HRID 859038노트

반응식

HRID 859038 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][N:15]=[C:14]([O:18][C:19]2[C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=[CH:21][CH:20]=2)[CH:13]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>C1(C)C=CC=CC=1>[C:29]([NH:28][C:26]1[S:27][C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([O:18][C:14]3[N:15]=[CH:16][N:17]=[C:12]([C:3]4[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:7][C:2]=4[NH:1][C:32](=[O:34])[CH3:33])[CH:13]=3)[C:24]=2[N:25]=1)(=[O:31])[CH3:30]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 21865046N-(4-(6-(2-Amino-4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

생성물 1

HCID 21865237N-{2-[6-(2-Acetylamino-benzothiazol-4-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenyl}-acetamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a suspension of N-{4-[6-(2-amino-4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide, (Example 151), (0.20 g, 0.50 mmol) in toluene (10 mL) was added acetic anhydride (0.090 g, 0.80 mmol, Aldrich). The reaction mixture was heated at reflux for 3 h, allowed to cool to room temperature and concentrated in vacuum. The residue was dissolved in EtOAc (20 mL) and washed with satd NaHCO3 (2×20 mL), dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (1:1:0.5 CH2Cl2/hexanes/EtOAc) provided the title compound as an off-white solid. Mp: 259–261° C. MS (ESI, pos. ion) m/z: 488 (M+1).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated in vacuum
  4. dissolutionThe residue was dissolved in EtOAc (20 mL)
  5. washwashed with satd NaHCO3 (2×20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customPurification by silica gel chromatography (1:1:0.5 CH2Cl2/hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-6b9a909429c840a286ab5ae1bd30984b
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148221B2

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