Sodium hydride → 2-{3-[4-(4-Methoxy-benzoyl)-piperidin-1-yl]-2-oxo-pyrrolidin-1-ylmethyl}-4a,7a-dihydro-3H-thieno[3,2-d]pyrimidin-4-one

HRID 1752267노트

반응식

HRID 1752267 반응식
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][NH:17][C:16]3=[O:20])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.Cl[CH2:24][C:25]1[NH:26][C:27](=[O:34])[C:28]2[S:33][CH:32]=[CH:31][C:29]=2[N:30]=1.[H-].[Na+]>C1COCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][N:17]([CH2:24][C:25]4[NH:26][C:27](=[O:34])[CH:28]5[S:33][CH:32]=[CH:31][CH:29]5[N:30]=4)[C:16]3=[O:20])[CH2:11][CH2:10]2)=[O:8])=[CH:21][CH:22]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 712122103-(4-(4-Methoxybenzoyl)piperidin-1-yl)pyrrolidin-2-oneHCID 1354161912-(chloromethyl)-3H,4H-thieno[3,2-d]pyrimidin-4-one

생성물 1

HCID 712123142-{3-[4-(4-Methoxy-benzoyl)-piperidin-1-yl]-2-oxo-pyrrolidin-1-ylmethyl}-4a,7a-dihydro-3H-thieno[3,2-d]pyrimidin-4-one수율 95.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a solution of 3-[4-(4-methoxy-benzoyl)-piperidin-1-yl]-pyrrolidin-2-one (0.165 mmol, 50 mg) and 2-chloromethyl-3H-thieno[3,2-d]pyrimidin-4-one (0.165 mmol, 33 mg) in THF (2 mL) was added sodium hydride (60%, 0.331 mmol, 23 mg) and heated to 70° C. for 1 hour. The reaction was allowed to cool to ambient temperature, diluted with 10 mL of ether, and the resulting solid in suspension was filtered and dried under vacuum provided the title compound as an off-white solid (70.5 mg, 95.4% yield). HRMS calculated for C24H26N4O4S 466.5632. found (ESI, [M+H]+) 467.1740. 1H NMR (400 MHz, MeOD) δ ppm 1.65-1.92 (m, 4H) 2.06-2.29 (m, 2H) 2.48-2.62 (m, 1H) 2.78-2.89 (m, 1H) 2.89-3.00 (m, 1H) 3.09-3.18 (m, 1H) 3.34-3.53 (m, 4H) 3.55-3.65 (m, 1H) 3.68-3.77 (m, 1H) 4.23-4.32 (m, 1H) 4.60-4.69 (m, 1H) 6.97 (d, J=9.03 Hz, 2H) 7.17-7.24 (m, 1H) 7.73-7.81 (m, 1H) 7.96 (d, J=9.03 Hz, 2H), analytical RP-HPLC retention time=2.77 min

후처리

  1. temperatureto cool to ambient temperature
  2. filtrationthe resulting solid in suspension was filtered
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-a8a3801c63ed46d48bbab0ed04eaa005
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163003B2

반응 노트

불러오는 중…