Methanol → HCID 118049778, compound

HRID 595867Notes

Reaction equation

[CH2:1]([NH:8][C:9](=[O:38])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:21]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:20][CH:19]=[C:18]([C@@H:29]3[CH2:34][CH2:33][CH2:32][C@@H:31]([S:35][CH3:36])[CH2:30]3)[N:17]=2)=[CH:12][C:11]=1[F:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-:52].[Na+].C[OH:55]>O.CCOC(C)=O>[CH2:1]([NH:8][C:9](=[O:38])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:21]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:20][CH:19]=[C:18]([C@@H:29]3[CH2:34][CH2:33][CH2:32][C@@H:31]([S:35]([CH3:36])(=[O:55])=[O:52])[CH2:30]3)[N:17]=2)=[CH:12][C:11]=1[F:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To trans racemate (+/−)-N-benzyl-2-fluoro-4-(6-((1R,3R)-3-(methylthio)cyclohexyl)-3-pivalamidopyrazin-2-yl)benzamide (35 mg, 0.065 mmol) in MeOH (327 μL) at 0° C. was added oxone (52.3 mg, 0.085 mmol) in water (327 μL). The reaction mixture was stirred at 0° C. and room temperature thereafter for 3 h. The reaction mixture was quenched by 2 equiv. of sodium thiosulfate (20.70 mg, 0.131 mmol) in 2 mL water at 0° C. Stirred for 30 min, and then basified by adding 6N NaOH at 0° C. Diluted with EtOAc, and dried over sodium sulfate three times. Then filtered and concentrated to afford 25 mg of (+/−)-N-benzyl-2-fluoro-4-(6-((1R,3R)-3-(methylsulfonyl)cyclohexyl)-3-pivalamidopyrazin-2-yl)benzamide in 67.4% yield which was taken to the next step without further purification. LCMS (m/z): 567.4 (MH+), 0.90 min.

Workup

stirringStirred for 30 min
dry with materialdried over sodium sulfate three times
filtrationThen filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-65a80b698fc844ed8b2e89e78d08640b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

Loading…