Water → HCID 44544091, compound

HRID 2387337Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([S:41]([CH2:44][CH3:45])(=[O:43])=[O:42])=[CH:12][C:13]=1[C:14]#[C:15][CH2:16][C:17]([OH:40])([C:36]([F:39])([F:38])[F:37])[CH2:18][C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](=[O:35])(=[O:34])[N:29]=CN(C)C)([CH3:21])[CH3:20])(C)(C)C.C1CCN2C(=NCCC2)CC1.O>CO>[CH2:44]([S:41]([C:11]1[CH:12]=[C:13]2[CH:14]=[C:15]([CH2:16][C:17]([OH:40])([C:36]([F:39])([F:37])[F:38])[CH2:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([NH2:29])(=[O:35])=[O:34])([CH3:21])[CH3:20])[NH:7][C:8]2=[CH:9][N:10]=1)(=[O:42])=[O:43])[CH3:45]

Participants

Conditions

Temperature: 70 °C

Procedure

To a vial was added {4-[6-(2-{[1-dimethylaminomethylidene]sulfamoyl}phenyl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]-6-ethanesulfonylpyridin-3-yl}carbamic acid tert-butyl ester (48 mg, 0.07 mmol) in 3 mL of methanol, followed by the addition of DBU (106 mg, 0.7 mmol). The reaction mixture was stirred at 70° C. for 90 minutes. To the reaction was added 0.5 mL of water, and the reaction mixture was stirred at 70° C. for 1.5 hours. The reaction mixture was concentrated in vacuo. The crude mixture was purified by flash chromatography. The column was eluted with 0-5% MeOH/CH2Cl2 to afford 18 mg (48%) of 2-[3-(5-ethanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl]benzenesulfonamide. MS (ES+) m/z 534 [M+H]+.

Workup

stirringthe reaction mixture was stirred at 70° C. for 1.5 hours
concentrationThe reaction mixture was concentrated in vacuo
customThe crude mixture was purified by flash chromatography
washThe column was eluted with 0-5% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-49b08bb30aea453682468ecf943447e0
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268859B2

Reaction notes

Loading…