Sulfamide → HCID 59249272, compound

HRID 1807119Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([F:45])=[C:11]([C@@H:15]2[C@:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[F:29])([C:20]#[N:21])[C@H:18]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH:17][C@H:16]2[C:35]([NH:37][C@H:38]2[CH2:43][CH2:42][C@H](N)[CH2:40][CH2:39]2)=[O:36])[CH:12]=[CH:13][CH:14]=1.[S:46]([NH2:50])([NH2:49])(=[O:48])=[O:47]>C1COCC1>[Cl:8][C:9]1[C:10]([F:45])=[C:11]([C@@H:15]2[C@:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[F:29])([C:20]#[N:21])[C@H:18]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH:17][C@H:16]2[C:35]([NH:37][CH:38]2[CH2:43][CH2:42][N:49]([S:46]([NH2:50])(=[O:48])=[O:47])[CH2:40][CH2:39]2)=[O:36])[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of rac-4-{[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-trans-cyclohexylamine trifluoroacetic acid salt (50 mg, 0.091 mmol) in THF (3 mL), sulfamide (Aldrich, 40 mg, 0.416 mmol) was added and the mixture was stirred at 110° C. for 25 min. on microwave oven. The reaction was quenched with addition of water. The mixture was extracted with EtOAc (2×10 mL) and the extracts were dried with magnesium sulfate. The solvent was removed and the residue was purified on a reverse phase HPLC (25-90, acetonitrile/water) to give a white solid. 49 mg.

Workup

customThe reaction was quenched with addition of water
extractionThe mixture was extracted with EtOAc (2×10 mL)
dry with materialthe extracts were dried with magnesium sulfate
customThe solvent was removed
customthe residue was purified on a reverse phase HPLC (25-90, acetonitrile/water)
customto give a white solid

Sources & evidence

ORD record: ord-cfc694e8a96c4edaa2ea4ddbb9d1afc6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354444B2

Reaction notes

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