Methyl iodide → HCID 22663244, compound

HRID 392200Notes

Reaction equation

[H-].[Na+].[CH:3]1([C:8]2[NH:9][C:10]3[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=[C:13]([O:21][CH3:22])[C:11]=3[N:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.I[CH3:24]>CN(C)C=O.C(OCC)C>[CH:3]1([C:8]2[N:12]([CH3:24])[C:11]3[C:13]([O:21][CH3:22])=[CH:14][CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:10]=3[N:9]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of sodium hydride (0.55 g, 60% dispersion in mineral oil) in dimethylformamide (1 ml), cooled to 0° C., was treated with a solution of methyl 2-cyclopentyl-7-methoxy-3H-benzimidazole-4-carboxylate [3.61 g, Reference Example 3(t)]) in dimethylformamide (34 ml). The resulting mixture was stirred for 40 minutes then treated with iodomethane (0.82 ml). The reaction mixture was allowed to stand at 4° C. for 2 days then diluted with diethyl ether, then washed with brine, then dried over magnesium sulphate and then evaporated. The residue was subjected to flash chromatography on silica to give methyl 2-cyclopentyl-7-methoxy-1-methyl-1H-benzimidazole-4-carboxylate (3.18 g), [NMR (CDCl3): δ 1.70(m, 2H), 1.90(m, 2H), 2.16(m, 4H), 3.25(m, 1H), 3.95(s, 6H), 4.00(s, 3H), 6.64(d, J=8 Hz, 1H), 7.89(d, J=8 Hz, 1H), and methyl 2-(cyclopentyl)-7-methoxy-3-methyl-3H-benzimidazole-4-carboxylate (0.37 g), [M+288, NMR (CDCl3): δ 1.70(m, 2H), 1.90(m, 2H), 2.14(m, 4H), 3.25(m, 1H) 3.92(s, 6H), 4.02(s, 3H), 6.64(d, J=8 Hz, 1H), 7.75(d, J=8 Hz, 1H)].

Workup

waitto stand at 4° C. for 2 days
washwashed with brine
dry with materialdried over magnesium sulphate
customevaporated

Sources & evidence

ORD record: ord-792fed854f4b45b482690a9d20dd2e36
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800645B1

Reaction notes

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