Benzo(d)thiazol-2-amine → tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1518264노트

반응식

HRID 1518264 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([C:18](O)=[O:19])[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH2:30].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH:30][C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17][CH2:16]2)=[O:19]

참가 물질

6

반응물 3

HCID 8706Benzo(d)thiazol-2-amineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 450740022-[(Tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

생성물 1

HCID 59447535tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate수율 84.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.8 g, 24.5 mmol) and benzo[d]thiazol-2-amine (5.52 g, 36.8 mmol) in DCM (80 mL) was added EDCI (9.4 g, 49.04 mmol) and DMAP (6 g, 49 mmol). The mixture was stirred at rt overnight. The reaction mixture was diluted with DCM (400 mL), washed with 5% aq. HCl, water, brine, dried over Na2SO4, and concentrated under reduced pressure to provide 8.5 g of the desired product tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1A): 1H NMR (300 MHz, CDCl3) δ ppm 7.83 (1H, m), 7.48 (1H, d), 7.34 (4H, m), 7.19 (1H, t), 4.91 (2H, m), 3.67 (2H, t), 2.92 (2H, t), 1.47 (9H, m). MS (ESI(+)): m/z 410 (M+H).

후처리

  1. washwashed with 5% aq. HCl, water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-65ee90fffa594355ac143d06117995c2
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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