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

HRID 2308268Notes

Reaction equation

HRID 2308268 reaction equation
[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].[C:24]([O-:27])([O-])=O.[K+].[K+].[CH3:30][C:31]#[N:32]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:19][C:18]1[CH:23]=[CH:14][C:15]([C:24]([NH:32][C:31]2[CH:30]=[CH:6][CH:5]=[CH:4][N:1]=2)=[O:27])=[CH:16][CH:17]=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]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 226013948-(2-Nitrobenzenesulfonyl)amino-5,6,7,8-tetrahydroquinoline

Product 1

HCID 226014464-{[(2-Nitrobenzenesulfonyl)(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-N-pyridin-2-yl-benzamideYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8-[N-(2-nitrobenzenesulfonyl)]amino-5,6,7,8-tetrahydroquinoline (230 mg, 0.69 mmol), 4-Chloromethyl-N-pyridinyl-2-yl-benzamide (170 mg, 0.69 mmol), and K2CO3 (285 mg, 2.06 mmol) were heated to reflux in CH3CN (3 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 6% ethyl acetate in CH2Cl2 afforded the title compound (344 mg, 92%) as white foam. 1NMR (CDCl3) δ 1.61-1.65 (m, 1H), 1.74-1.86 (m, 2H), 2.33-2.37 (m, 1H), 2.59-2.65 (m, 2H), 3.92 (d, 1H, J=16.2), 4.87 (d, 1H, J=16.5 Hz), 5.32 (dd, 1H, J=5.8, 11.3 Hz), 7.04-7.11 (m, 2H), 7.31-7.37 (m, 3H), 7.49-7.67 (m, 3H), 7.73-7.80 (m, 3H), 8.15 (d, 1H, J=7.8 Hz), 8.22 (d, 1H, J=4.2 Hz), 8.31 (d, 1H, J=4.2 Hz), 8.35 (d, 1H, J=8.4 Hz), 8.45 (br, s, 1H); ES-MS m/z 544.1 (M+H).

Workup

  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 using 6% ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-ae30f2e399ae404896877a2dbf354c80
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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