Water → HCID 11721247, compound

HRID 1715103Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:11]([CH3:23])=[C:12]([C:14]([NH:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[N:13]=1.C(N(CC)CC)C.[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([S:44](Cl)(=[O:46])=[O:45])[CH:39]=1.O>ClCCl>[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([S:44]([O:30][C:27]2[CH:26]=[CH:25][C:24]([N:10]3[C:11]([CH3:23])=[C:12]([C:14]([NH:16][N:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[O:15])[N:13]=[C:9]3[C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[CH:29][CH:28]=2)(=[O:46])=[O:45])[CH:39]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(2,4-Dichlorophenyl)-1-(4-hydroxyphenyl)-5-methyl-N-piperidin-1-yl-1H-imidazole-4-carboxamide, prepared as described in Ex. 2, Step 1 (100 mg, 0.22 mmol) and triethylamine (0.31 ml, 2.25 mmol) in dichloromethane (5.0 ml) were cooled to −78° C. 3-Pyridinesulfonyl chloride (144 mg, 0.67 mmol) was added in small portions to the reaction mixture. The resulting mixture was stirred at −78° C. for 1 h, and at room temperature overnight. Water was added to the reaction, the phases were separated and the organic phase washed with water and dried. The solvent was removed under reduced pressure and separation by preparatory HPLC gave the title compound (110 mg, 84%) as a solid.

Workup

customat room temperature
customovernight
customthe phases were separated
washthe organic phase washed with water
customdried
customThe solvent was removed under reduced pressure and separation by preparatory HPLC

Sources & evidence

ORD record: ord-6e8d2f0f160748899a07688c4c74b22b
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799804B2

Reaction notes

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