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

HRID 474308

반응식

HRID 474308 반응식
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:3]=1[CH2:4][C:5]1[S:6][C:7]2[N:8]=[C:9](S(C)(=O)=O)[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.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(O)(CC)(C)C>[Cl:33][C:29]1[CH:30]=[CH:31][CH:32]=[C:2]([Cl:1])[C:3]=1[CH2:4][C:5]1[S:6][C:7]2[N:8]=[C:9]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[N:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=3)[C:12]=2[N:13]=1

참가 물질

4

반응물 2

HCID 8083MorpholineHCID 42641464[2-(2,6-Dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

생성물 1

HCID 42641465[2-(2,6-Dichloro-benzyl)-5-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine수율 77%

시약·촉매·용매 1

HCID 64052-Methyl-2-butanol용매

반응 조건

온도
130 °C

실험 절차

To a mixture of [2-(2,6-dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine (49 mg, 0.1 mmol) in tert-amyl alcohol (2 mL) was added morpholine (24 mg, 0.3 mmol). The resulting mixture was heated to 130° C. in a sealed tube. After 12 h, the solution was cooled and purified by preparative reverse-phase HPLC to afford the title compound as a colorless solid (37 mg, 77%). MS (ESI): mass calcd. for C23H18Cl2F3N5OS, 539.0; m/z found, 540.0 [M+H]+. 1H NMR ((CD3)2SO): 10.14 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.70 (d, J=8.6 Hz, 2H), 7.61 (d, J=8.1 Hz, 2H), 7.49-7.42 (m, 1H), 4.69 (s, 2H), 3.66 (s, 8H).

후처리

  1. temperaturethe solution was cooled
  2. custompurified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-ef391451dd594d7f91ea1601bec05317
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637527B2

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