Succinic anhydride → 1-[4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]pyrrolidine-2,5-dione

HRID 885975노트

반응식

HRID 885975 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:14](=[O:22])[NH:15][C:16]([CH3:21])([CH3:20])[CH2:17][C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.[C:24]1(=O)[O:29][C:27](=[O:28])[CH2:26][CH2:25]1>CN(C=O)C>[CH3:20][C:16]1([CH3:21])[NH:15][C:14](=[O:22])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([N:1]5[C:27](=[O:28])[CH2:26][CH2:25][C:24]5=[O:29])[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1

참가 물질

4

반응물 2

HCID 7922Succinic anhydrideHCID 584416902-(6-amino-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,7-dihydro-6,6-dimethylthiazolo[5,4-c]pyridin-4(5H)-one

생성물 1

HCID 671861051-[4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]pyrrolidine-2,5-dione수율 34%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
140 °C

실험 절차

A mixture of Example 42 (50 mg, 0.15 mmol) and succinic anhydride (20 mg, 0.15 mmol) in DMF (4 mL) was stirred at 140° C. under microwave irradiation for 1 h. The reaction mixture was concentrated in vacuo, dissolved in acetic acid and stirred at 140° C. under microwave irradiation for 1 h. It was concentrated in vacuo and purified by preparative HPLC (Method 7) to give the title compound (21 mg, 34%) as an off-white solid. δH (CDCl3) 8.05 (1H, d, J 2.1 Hz), 7.11-6.91 (2H, m), 5.45 (1H, s), 4.41-4.32 (2H, m), 4.19-4.10 (2H, m), 2.92 (4H, s), 2.88 (2H, s), 1.39 (6H, s). LCMS (ES+) 413.0 (M+H)+, RT 2.58 minutes (Method 2).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in acetic acid
  3. concentrationIt was concentrated in vacuo
  4. custompurified by preparative HPLC (Method 7)

출처 및 근거

ORD 기록
ord-f0a5a4ed4f5748e6bd10dfb6dbf3a57b
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242116B2

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