Pyridine → HCID 59303068, compound

HRID 1692133Notes

Reaction equation

Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[C:23]2[N:27]([C@H:28]3[CH2:32][CH2:31][NH:30][CH2:29]3)[CH:26]=[N:25][N:24]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].N1C=CC=CC=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C1COCC1>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[C:23]2[N:27]([C@H:28]3[CH2:32][CH2:31][N:30]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:29]3)[CH:26]=[N:25][N:24]=2)(=[O:13])=[O:14])=[CH:8][CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To 4-tert-butyl-N-[4-chloro-2-((S)-4-pyrrolidin-3-yl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide hydrochloride (0.25 g, 0.505 mmol) in THF (8 mL) was added pyridine (0.60 mL, 7.4 mmol). The resultant solution was stirred for 20 minutes at room temperature. The reaction mixture was subsequently cooled to 0° C., methanesulfonyl chloride (0.595 mL, 7.6 mmol) was added, and the mixture was stirred overnight at room temperature. The following day, the volatiles were evaporated and the resultant residue was adsorbed onto silica gel and purified by automated normal-phase chromatography (using 50→100% EtOAc in hexanes) to obtain the title compound (0.183 g) in 67.5% yield: MS (ES) M+H expected 538.0, found 538.1.

Workup

customThe following day, the volatiles were evaporated
custompurified by automated normal-phase chromatography (using 50→100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-b187395136ed4ee19c9a93e960c5a41f
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153818B2

Reaction notes

Loading…