Sodium hydride → 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-ethyl-1H-pyrrole-3-carboxamide

HRID 1435442Notes

Reaction equation

HRID 1435442 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].[C:13]([C:17]1[N:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:20]2[CH:29]=[CH:30][C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:32][C:19]=2[N:18]=1)([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[C:13]([C:17]1[N:21]([CH2:22][CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[C:20]2[CH:29]=[CH:30][C:31]([S:33]([N:8]3[CH:9]=[CH:10][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:7]3)(=[O:34])=[O:35])=[CH:32][C:19]=2[N:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 55284999N-ethyl-1H-pyrrole-3-carboxamideHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 236601121-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-ethyl-1H-pyrrole-3-carboxamideYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure in Example 29, using N-ethyl-1H-pyrrole-3-carboxamide (2.7 g, 20 mmol) (see following step B for preparation), sodium hydride (4.0 g, 60%, 100 mmol) and 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (6.1 g, 16 mmol) in THF (250 mL). The crude product was purified by MPLC using Hex/EtOAc (1:4) on silica gel to give 4.0 g (53%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.13 (t, J=7.23 Hz, 3 H), 1.41-1.58 (m, 4 H), 1.61 (s, 9 H), 2.24-2.38 (m, 1 H), 3.24-3.35 (m, 4 H), 3.85-3.94 (m, 2 H), 4.44 (d, J=7.42 Hz, 2 H), 6.65 (dd, J=3.32, 1.56 Hz, 1 H), 7.29 (dd, J=3.32, 2.34 Hz, 1 H), 7.77-7.82 (m, 1 H), 7.95-7.98 (m, 2 H), 8.24-8.30 (m, 1 H); MS (ESI) (M+H)+=472.8; Anal. Calcd for C24H32N4O4S+1.20 TFA+0.10 EtOAc+0.30H2O (624.86): C, 51.71; H, 5.58; N, 8.97. Found: C, 51.73; H, 5.66; N, 8.91.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-8e976b1fdf6e4611a647cad856186ffc
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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