Potassium Carbonate → 4-{[(2-Nitrobenzenesulfonyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-pyridin-2-ylmethyl-benzamide

HRID 970890노트

반응식

HRID 970890 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH:14]1[C:23]2[N:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15]1)(=[O:12])=[O:11])([O-:3])=[O:2].Cl[CH2:25][C:26]1[CH:41]=[CH:40][C:29]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[O:31])=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[O:31])=[CH:40][CH:41]=1)[CH:14]1[C:23]2[N:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15]1)(=[O:11])=[O:12])([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 226012774-Chloromethyl-N-pyridin-2-ylmethyl-benzamideHCID 226013948-(2-Nitrobenzenesulfonyl)amino-5,6,7,8-tetrahydroquinoline

생성물 1

HCID 226013714-{[(2-Nitrobenzenesulfonyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-pyridin-2-ylmethyl-benzamide수율 90.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

8-(2-nitrobenzenesulfonyl)amino-5,6,7,8-tetrahydroquinoline (402 mg, 1.20 mmol), 4-Chloromethyl-N-pyridin-2-ylmethyl-benzamide (314 mg, 1.20 mmol), and K2CO3 (498 mg, 3.60 mmol) were heated to reflux in CH3CN (4 mL) for 24 hours under N2. The reaction mixture was diluted with 200 mL ethyl acetate, and washed with sat. NaHCO3, then brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by flash chromatography on silica gel, using 50% ethyl acetate in CH2Cl2, afforded the title compound (603 mg, 90%) as white foam. 1H NMR (CDCl3) δ 1.56-1.61 (m, 1H), 1.74-2.05 (m, 2H), 2.32-2.36 (m, 1H), 2.58-2.64 (m, 2H), 3.95 (d, 1H, J=16.2 Hz), 4.74 (d, 2H, J=4.5 Hz), 4.85 (d, 1H, J=15.9 Hz), 5.30 (dd, 1H, J=11.1, 17.4 Hz), 7.05 (dd, 1H, J=4.5, 7.5 Hz), 7.22-7.29 (m, 2H), 7.34 (dd, 2H, J=7.5, 7.8 Hz), 7.48-7.73 (m, 8H), 8.12-8.15 (m, 1H), 8.20-8.24 (m, 1H), 8.45-8.59 (m, 1H); ES-MS m/z 558.2 (M+H).

후처리

  1. washwashed with sat. NaHCO3
  2. dry with materialbrine and dried over Na2SO4
  3. customEvaporation of the solvent and purification of the residue by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-af42d369c43540d4958cb0bebc3db52d
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312234B2

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