Diisopropylethylamine → Benzothiazol-2-yl-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-methanone

HRID 1931759노트

반응식

HRID 1931759 반응식
FC(F)(F)C(O)=O.[CH3:8][S:9]([C:12]1[CH:33]=[CH:32][C:15]([O:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[N:24]=[CH:25][C:18]=23)=[CH:14][CH:13]=1)(=[O:11])=[O:10].[S:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[C:35]1[C:43](Cl)=[O:44].C(N(C(C)C)CC)(C)C>ClCCl>[S:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[C:35]1[C:43]([N:29]1[CH2:28][CH2:27][CH:26]([N:23]2[C:19]3=[N:20][CH:21]=[N:22][C:17]([O:16][C:15]4[CH:14]=[CH:13][C:12]([S:9]([CH3:8])(=[O:11])=[O:10])=[CH:33][CH:32]=4)=[C:18]3[CH:25]=[N:24]2)[CH2:31][CH2:30]1)=[O:44]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2776254Benzothiazole-2-carbonyl chlorideHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2회

생성물 1

HCID 57964911Benzothiazol-2-yl-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-methanone수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 27; 63 mg, 0.13 mmol), benzothiazole-2-carbonyl chloride (available from Alfa Aesar, Ward Hill, Mass., USA; 33 mg, 0.17 mmol), and diisopropylethylamine (0.14 mL, 0.8 mmol) in dry dichloromethane (4 mL) was stirred at room temperature over the weekend. The solution was diluted with dichloromethane (6 mL) and washed with 1 M aqueous hydrochloric acid (5 mL), water (5 mL), saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL). The organic layer was evaporated and the crude product was purified by HPLC to give benzothiazol-2-yl-{4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-methanone (43 mg, 62%) as a light yellow solid.

후처리

  1. washwashed with 1 M aqueous hydrochloric acid (5 mL), water (5 mL), saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL)
  2. customThe organic layer was evaporated
  3. customthe crude product was purified by HPLC

출처 및 근거

ORD 기록
ord-a58be4217de44c15b1b6d19ed8298491
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

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