Piperidine → HCID 67195137, compound

HRID 1893849Notes

Reaction equation

HRID 1893849 reaction equation
[C:1]([C@@H:4]([N:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH:29]=[CH2:30])=[CH:23][CH:22]=1)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:3])[NH2:2].[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C1(C)C=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([N:9]([C@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:1]([NH2:2])=[O:3])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH2:29][CH2:30][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:23][CH:22]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 67197466HCID 67197466, compound

Product 1

HCID 67195137HCID 67195137, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(4-{[N-((1S)-1-carbamoyl-3-methyl-butyl)-N-(4-chlorobenzenesulfonyl)amino]-methyl}-phenyl)-acrylamide (0.10 g, 0.22 mmol) in toluene (5 mL) was added piperidine (20 mg, 0.24 mmol). The mixture was heated at a gentle reflux for 1 h and then the solvent was removed in vacuo. Purification by flash chromatography (SiO2, 10% MeOH/CH2Cl2) afforded the title compound (105 mg) in 86% yield. MS (ESI), (M+H)+449.16, 1H NMR (CDCl3, 400 MHz) δ 7.69 (d, 2H, J=8.0), 7.63 (d, 2H, J=8.0), 7.38 (d, 2H, J=8.0), 7.23 (d, 2H, J=8.0), 6.25 (br s, 1H), 5.35 (br s, 1H), 4.75 (d, 1H, Jab=16), 4.38 (d, 1H, Jab=16), 3.25 (t, 1H, J=6.0), 2.65 (t, 2H, J=6.0), 2.56-2.44 (m, 6H), 1.95 (m, 1H), 1.68-1.45 (m, 8H), 0.98 (d, 3H, J=7.0), 0.94 (d, 3H, J=7.0).

Workup

  1. temperatureThe mixture was heated at
  2. temperaturea gentle reflux for 1 h
  3. customthe solvent was removed in vacuo
  4. customPurification by flash chromatography (SiO2, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8f38868eb7894b8a99b95283bd6f4ae3
Source dataset
uspto-grants-2013_08
Patent number
US08513253B2

Reaction notes

Loading…