Triethylamine → 3-{1-[(1,2-dimethyl-1H-imidazol-5-yl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

HRID 2267588Notes

Reaction equation

HRID 2267588 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[C:30]([S:31](Cl)(=[O:33])=[O:32])=[CH:29][N:28]=[C:27]1[CH3:35].C(N(CC)CC)C>>[CH3:25][N:26]1[C:30]([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])=[CH:29][N:28]=[C:27]1[CH3:35]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27362581,2-dimethyl-1H-imidazole-5-sulfonyl chlorideHCID 114271625-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 590033383-{1-[(1,2-dimethyl-1H-imidazol-5-yl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Procedure

Following the general procedure in example 267, 5-(phenyl)-3-(4-piperidinyl)-1H-indole-7-carboxamide (72 mg, 0.22 mmol), 1,2-dimethyl-1H-imidazole-5-sulfonyl chloride (64.2 mg, 0.33 mmol) and triethylamine (0.13 mL, 0.66 mmol) were reacted to form the desired product which was purified by Gilson HPLC (CH3CN/Water, 0.1% TFA) (48.3 mg, 45%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ba2ed16773d64adfb7384449a282ed83
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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