Methanol → N-(5-{4-[(4-methylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-1,3-thiazol-2-yl)acetamide

HRID 473853노트

반응식

HRID 473853 반응식
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](Cl)=[O:9])[CH2:4][CH2:3]1.Cl.[O:12]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[S:27][C:26]([NH:28][C:29](=[O:31])[CH3:30])=[N:25][CH:24]=3)=[CH:22][C:17]=2[CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C)C=O>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:15]2[CH2:16][C:17]3[CH:22]=[C:21]([C:23]4[S:27][C:26]([NH:28][C:29](=[O:31])[CH3:30])=[N:25][CH:24]=4)[CH:20]=[CH:19][C:18]=3[O:12][CH2:13][CH2:14]2)=[O:9])[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 152215164-Methylpiperidine-1-carbonyl ChlorideHCID 86647837N-[5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide hydrochloride

생성물 1

HCID 49833483N-(5-{4-[(4-methylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-1,3-thiazol-2-yl)acetamide수율 64,150.898%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Methylpiperidine-1-carbonyl chloride (reagent preparation 37) (103 mg, 0.64 mmol) was added to a mixture of N-[5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide hydrochloride, (173 mg, 0.53 mmol) and potassium carbonate (374 mg, 2.7 mmol) in N,N-dimethylformamide (2 mL). The resulting mixture was stirred at room temperature for 18 hours, then methanol (2 mL) was added and concentrated. The residue was diluted with ethyl ether (40 mL), a solid was collected by filtration, and washed with ether and water to give N-(5-{4-[(4-methylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-1,3-thiazol-2-yl)acetamide (140 mg, 0.34 mol, 63% yield), 1H NMR (400 MHz, DMSO-d6): 7.58 (s, 1H), 7.35 to 7.32 (m, 2H), 6.91 (d, 1H), 4.36 (s, 2H), 4.12 (br, 2H), 3.54 to 3.47 (m, 4H), 2.71 to 2.65 (m, 2H), 2.00 (s, 3H), 1.60 to 1.43 (m, 3H), 1.16 to 1.067 (m, 2H), 0.92 (d, 3H); MS (EI) for C21H26N4O3S: 415 (MH+).

후처리

  1. concentrationconcentrated
  2. additionThe residue was diluted with ethyl ether (40 mL)
  3. filtrationa solid was collected by filtration
  4. washwashed with ether and water

출처 및 근거

ORD 기록
ord-859d2eecb5614996a8b710465c633ad6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637499B2

반응 노트

불러오는 중…