Tetrahydrofuran → [2-(2,6-Dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

HRID 60200

반응식

HRID 60200 반응식
[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:3]=1[CH2:4][C:5]1[S:6][C:7]2[N:8]=[C:9](SC)[N:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:12]=2[N:13]=1.[S:32]([O-:37])(O[O-])(=O)=[O:33].[K+].[K+].[CH2:40]1COCC1>CO.O>[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:3]=1[CH2:4][C:5]1[S:6][C:7]2[N:8]=[C:9]([S:32]([CH3:40])(=[O:37])=[O:33])[N:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=3)[C:12]=2[N:13]=1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 10313463Potassium peroxymonosulphateHCID 42642138HCID 42642138, 화합물

생성물 1

HCID 42641464[2-(2,6-Dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine수율 85%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

To a solution of [2-(2,6-dichloro-benzyl)-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine (110 mg, 0.22 mmol) in THF (6 mL) and MeOH (6 mL) was added a solution of potassium peroxymonosulfate (406 mg, 0.66 mmol) in H2O (6 mL). The resulting mixture was stirred vigorously at 40° C. After 24 h, the mixture was concentrated and the crude residue was diluted with satd. aq. NaHCO3 (10 mL) and extracted with EtOAc (10 mL×3). The combined organic layers were dried, concentrated, and purified by FCC to afford a colorless solid (100 mg, 85%). MS (ESI): mass calcd. for C20H13Cl2F3N4O2S2, 531.9; m/z found, 532.9 [M+H]+. 1H NMR ((CD3)2SO): 11.02 (s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.77 (d, J=8.7 Hz, 2H), 7.64 (d, J=8.1 Hz, 2H), 7.50 (dd, J=8.5, 7.8 Hz, 1H), 4.89 (s, 2H), 3.37 (s, 3H).

후처리

  1. concentrationthe mixture was concentrated
  2. additionthe crude residue was diluted with satd
  3. extractionaq. NaHCO3 (10 mL) and extracted with EtOAc (10 mL×3)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. custompurified by FCC

출처 및 근거

ORD 기록
ord-3af7cce02cdd495bbb65d50b45a8dbd9
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440978B2

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