Triethylamine → 3-{1-[(1-methyl-1H-imidazol-4-yl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

HRID 2267577Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][N:26]1[CH:30]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[N:28]=[CH:27]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:25][N:26]1[CH:30]=[C:29]([S:31]([N:22]2[CH2:23][CH2:24][CH:19]([C:10]3[C:9]4[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:8]=4)[NH:12][CH:11]=3)[CH2:20][CH2:21]2)(=[O:33])=[O:32])[N:28]=[CH:27]1

Participants

Conditions

Temperature: 0 °C

Procedure

To 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (40 mg, 0.12 mmol) in methylene chloride (5 mL) at 0° C., 1-methyl-1H-imidazole-4-sulfonyl chloride (27.1 mg, 0.14 mmol) and triethylamine (0.07 mL, 0.50 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min. Then the reaction mixture was partitioned between methylene chloride and water, the aqueous layer was extracted with methylene chloride (25 mL×2) and combined organic phase was dried with Mg2SO4 and concentrated by reduce pressure, and purified by Gilson HPLC (reverse phase, eluting with CH3CN/Water, 0.1% TFA, 10/90, v/v, over 15 min) to give the title compound (22.5 mg, 39%).

Workup

customThen the reaction mixture was partitioned between methylene chloride and water
extractionthe aqueous layer was extracted with methylene chloride (25 mL×2)
dry with materialwas dried with Mg2SO4
concentrationconcentrated
custompurified by Gilson HPLC (reverse phase, eluting with CH3CN/Water, 0.1% TFA, 10/90, v/v, over 15 min)

Sources & evidence

ORD record: ord-f0d568c804a8442eb661f52e3fe9ee29
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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