Methyl isonipecotate → HCID 57937343, compound

HRID 1435482Notes

Reaction equation

HRID 1435482 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:25]1[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:26]1>CN(C1C=CN=CC=1)C.CC#N>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21]([N:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 424914Methyl isonipecotateHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937343HCID 57937343, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (400 mg, 0.98 mmol) was added to a solution of methyl piperidine-4-carboxylate (703 mg, 4.90 mmol) and DMAP (600 mg, 4.90 mmol) in MeCN (50 mL). The reaction mixture was stirred overnight at ambient temperature and the solvent was concentrated. The product was purified by MPLC using 50-90% EtOAc/Heptane on silica gel to provide the title compound as colorless oil. Yield: 182 mg (38%); 1H NMR (400 MHz, CDCl3) δ 1.48-1.57 (m, 4 H), 1.59 (s, 9 H), 1.76-1.89 (m, 2 H), 1.91-2.00 (m, 2 H), 2.17-2.34 (m, 2 H), 2.48 (td, J=11.28, 2.83 Hz, 2 H), 3.27-3.39 (m, 2 H), 3.64 (s, 3 H), 3.65-3.70 (m, 1 H), 3.95-4.04 (m, 2 H), 4.25 (d, J=7.42 Hz, 2 H), 7.42 (dd, J=8.59, 0.59 Hz, 1 H), 7.64 (dd, J=8.40, 1.76 Hz, 1 H), 8.17 (dd, J=1.66, 0.49 Hz, 1 H); MS (ESI) (M+H)+=478.0.

Workup

  1. concentrationthe solvent was concentrated
  2. customThe product was purified by MPLC

Sources & evidence

ORD record
ord-6ed3193a9d8647e1bec2f7bbb0981c94
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…