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

HRID 1435474Notes

Reaction equation

HRID 1435474 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+].[CH3:13][C:14]([C:18]1[N:22]([CH2:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:21]2[CH:30]=[CH:31][C:32]([S:34](Cl)(=[O:36])=[O:35])=[CH:33][C:20]=2[N:19]=1)([CH3:17])[CH2:15][CH3:16]>C1COCC1>[CH3:17][C:14]([C:18]1[N:22]([CH2:23][CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[C:21]2[CH:30]=[CH:31][C:32]([S:34]([N:8]3[CH:9]=[CH:10][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:7]3)(=[O:36])=[O:35])=[CH:33][C:20]=2[N:19]=1)([CH3:13])[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 55284999N-ethyl-1H-pyrrole-3-carboxamideHCID 579373072-tert-pentyl-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazole-5-sulfonyl chloride

Product 1

HCID 236606641-{[2-(1,1-Dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-ethyl-1H-pyrrole-3-carboxamideYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure in Example 29, using N-ethyl-1H-pyrrole-3-carboxamide (166 mg, 1.2 mmol) (see the step B in example 31 for preparation), sodium hydride (240 mg, 60%, 6.0 mmol) and 2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (385 mg, 1.0 mmol) in THF (20 mL). The crude product was purified by MPLC using EtOAc on silica gel to give 195 mg (40%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.78 (t, J=7.42 Hz, 3 H), 1.13 (t, J=7.23 Hz, 3 H), 1.41-1.56 (m, 4 H), 1.59 (s, 6 H), 1.95 (q, J=7.49 Hz, 2 H), 2.21-2.35 (m, 1 H), 3.24-3.34 (m, 4 H), 3.85-3.94 (m, 2 H), 4.42 (d, J=7.62 Hz, 2 H), 6.65 (dd, J=3.32, 1.76 Hz, 1 H), 7.29 (dd, J=3.32, 2.34 Hz, 1 H), 7.78-7.82 (m, 1 H), 7.92 (d, J=8.8 Hz, 1 H), 7.96 (dd, J=8.8, 1.8 Hz, 1 H), 8.27 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=487.0; Anal. Calcd for C25H34N4O4S+110 TFA+0.1H2O (602.46): C, 53.83; H, 5.89; N, 9.30. Found: C, 53.79; H, 6.00; N, 9.19.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-91aa908a0bbd4accbbb34761e88988bd
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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