Sodium Iodide → ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-iodopropyl)thiazole-4-carboxylate

HRID 1518270노트

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HRID 1518270 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:33][CH2:34][CH2:35]Cl)=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[I-:37].[Na+]>C(#N)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:33][CH2:34][CH2:35][I:37])=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

참가 물질

4

반응물 2

HCID 5238Sodium IodideHCID 59447646ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-chloropropyl)thiazole-4-carboxylate

생성물 1

HCID 59447467ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-iodopropyl)thiazole-4-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
90 °C

실험 절차

To ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-chloropropyl)thiazole-4-carboxylate (2B) (9.3 g, 17.2 mmol) in acetonitrile (125 mL) was added sodium iodide (25.8 g, 172 mmol). The reaction mixture was purged with nitrogen twice. The reaction mixture was then heated at 90° C. for 5 hours, cooled to rt, and concentrated under reduced pressure. The concentrate was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was slurried in Et2O, filtered, washed with additional Et2O and dried under reduced pressure to provide the desired product ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-iodopropyl)thiazole-4-carboxylate (2C) in 93% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.89 (1H, s), 8.04 (1H, d), 7.79 (1H, d), 7.66 (1H, d), 7.43 (4H, m), 4.83 (2H, s), 4.19 (2H, q), 3.72 (2H, t), 3.26 (2H, t), 3.06 (4H, m), 2.03 (2H, m), 1.21 (3H, t).

후처리

  1. customThe reaction mixture was purged with nitrogen twice
  2. temperaturecooled to rt
  3. concentrationconcentrated under reduced pressure
  4. additionThe concentrate was diluted with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. filtrationfiltered
  10. washwashed with additional Et2O
  11. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-f6c3b79b41a44f009492ec7ebaf28cb8
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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