Ethyl nipecotate → HCID 57937350, compound

HRID 1435484Notes

Reaction equation

HRID 1435484 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][CH2:28][CH:27]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[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][CH2:28][CH:27]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[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 98969Ethyl nipecotateHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937350HCID 57937350, 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 ethyl piperidine-3-carboxylate (771 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 1.26 (t, J=7.13 Hz, 3 H), 1.29-1.38 (m, 1 H), 1.49-1.57 (m, 4 H), 1.59 (s, 9 H), 1.63-1.83 (m, 2 H), 1.91-2.02 (m, 1 H), 2.30 (td, J=11.43, 2.93 Hz, 2 H), 2.44 (t, J=11.13 Hz, 1 H), 2.57-2.69 (m, 1 H), 3.28-3.40 (m, 2 H), 3.65-3.75 (m, 1 H), 3.91 (dd, J=11.82, 3.81 Hz, 1 H), 3.96-4.05 (m, 2 H), 4.13 (q, J=7.03 Hz, 2 H), 4.25 (d, J=7.23 Hz, 2 H), 7.43 (d, J=8.20 Hz, 1 H), 7.64 (dd, J=8.59, 1.76 Hz, 1 H), 8.19 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+ 491.9.

Workup

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

Sources & evidence

ORD record
ord-42fc159f79dc448b973940b7be812af8
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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