Methyl pyrrolidine-3-carboxylate hydrochloride → HCID 57937292, compound

HRID 1435493Notes

Reaction equation

HRID 1435493 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].Cl.[CH3:26][O:27][C:28]([CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)=[O:29]>ClCCCl>[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:32]3[CH2:33][CH2:34][CH:30]([C:28]([O:27][CH3:26])=[O:29])[CH2:31]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 19261352Methyl pyrrolidine-3-carboxylate hydrochlorideHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937292HCID 57937292, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (1.21 g, 3.26 mmol) in DCL (25 mL) was slowly added to a solution of 3-(methoxycarbonyl)pyrrolidine hydrochloride (0.46 g, 3.58 mmol) and DIPLA (5.6 mL, 32.6 mmol) in DCE (80 mL). The reaction mixture was stirred for 3 h and the solvent was concentrated. The product was purified by MPLC on silica gel using EtOAc as eluent to provide the title compound as white solid. Yield: 0.60 g (39%); 1H NMR (400 MHz, CDCl3) δ 1.49-1.56 (m, 3 H), 1.55-1.58 (m, 1 H), 1.59 (s, 9 H), 1.93-2.13 (m, 2 H), 2.20-2.36 (m, 1 H), 2.89-3.01 (m, 1 H), 3.28-3.41 (m, 5 H), 3.60 (s, 3 H), 3.61-3.66 (m, 1 H), 3.94-4.06 (m, 2 H), 4.25 (d, J=7.42 Hz, 2 H), 7.44 (dd, J=8.50, 0.49 Hz, 1 H), 7.72 (dd, J=8.59, 1.76 Hz, 1 H), 8.24 (dd, J=1.76, 0.59 Hz, 1 H); MS (ESI) (M+H)+=464.0.

Workup

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

Sources & evidence

ORD record
ord-c808251f22724028a3428e0faa362160
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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