Ammonia → HCID 58920133, compound

HRID 1365501Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([F:31])[CH:22]=2)([NH:14][S@@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH2:9][C:10]([O:12]C)=O)=[N:6][CH:7]=1.[NH3:32]>C(O)CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([F:31])[CH:22]=2)([NH:14][S@@:15]([C:17]([CH3:18])([CH3:19])[CH3:20])=[O:16])[CH2:9][C:10]([NH2:32])=[O:12])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 180 °C

Procedure

(S)-methyl 3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-3-((R)-2-methylpropan-2-ylsulfinamido)propanoate (0.10 g, 0.20 mmol) was dissolved in 8N NH3 solution in ethylene glycol (1 mL) in a microwave vial. The reaction mixture was heated to 180° C. for 300 sec, the pressure was cautiously vented and the reaction mixture purified directly by prep HPLC (YMC ODSA30×100 mm, 0-100% over 10 min, MeOH/H2O/0.1% TFA). (S)-3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-3-((R)-2-methylpropan-2-ylsulfinamido)propanamide was isolated as a white solid (0.041 g, 41% yield) LCMS: 1.85 min [M+1] 466.1 (2 min gradient, MeOH/H2O 0.1% TFA). Starting material was also recovered (0.055 g, 55% recovered yield).

Workup

customthe reaction mixture purified directly by prep HPLC (YMC ODSA30×100 mm, 0-100% over 10 min, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record: ord-8e4e79ede397432c8d3dfcab71adeaea
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888376B2

Reaction notes

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