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

HRID 1435476Notes

Reaction equation

HRID 1435476 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[CH:11]=[CH:10][NH:9][CH:8]=1)=[O:6])([CH3:3])[CH3:2].[H-].[Na+].[CH3:14][C:15]([C:19]1[N:23]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:22]2[CH:31]=[CH:32][C:33]([S:35](Cl)(=[O:37])=[O:36])=[CH:34][C:21]=2[N:20]=1)([CH3:18])[CH2:16][CH3:17]>C1COCC1>[CH3:18][C:15]([C:19]1[N:23]([CH2:24][CH:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[C:22]2[CH:31]=[CH:32][C:33]([S:35]([N:9]3[CH:10]=[CH:11][C:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])=[CH:8]3)(=[O:37])=[O:36])=[CH:34][C:21]=2[N:20]=1)([CH3:14])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 579373072-tert-pentyl-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazole-5-sulfonyl chlorideHCID 57937383HCID 57937383, compound

Product 1

HCID 236608271-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-isopropyl-1H-pyrrole-3-carboxamideYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure in Example 29, using N-isopropyl-1H-pyrrole-3-carboxamide (76 mg, 0.50 mmol) (see following step B for preparation), sodium hydride (159 mg, 60%, 3.97 mmol) and 2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (535 mg, 1.39 mmol) in THF (15 mL). The crude product was purified by MPLC using Hex/EtOAc (3:7) on silica gel to give 158 mg (64%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.77 (t, J=7.42 Hz, 3 H), 1.15 (d, J=6.64 Hz, 6 H), 1.39-1.56 (m, 4 H), 1.59 (s, 6 H), 1.94 (q, J=7.42 Hz, 2 H), 2.19-2.38 (m, 1 H), 3.23-3.35 (m, 2 H), 3.83-3.96 (m, 2 H), 4.01-4.15 (m, 1 H), 4.41 (d, J=7.62 Hz, 2 H), 6.67 (dd, J=3.32, 1.56 Hz, 1 H), 7.28 (dd, J=3.12, 2.34 Hz, 1 H), 7.79-7.86 (m, 1 H), 7.88-7.99 (m, 2 H) 8.26 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=501.3; Anal. Calcd for C26H36N4O4S+1.2 TFA+0.1H2O (615.50): C, 55.33; H, 6.11; N, 9.09. Found: C, 55.38; H, 6.16; N, 9.04.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-68001f28fe464d68a0355cde2091e2a3
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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