Potassium Carbonate → HCID 72243991, compound

HRID 1807136Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[F:20])[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[F:30])([C:21]#[N:22])[CH:10]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[NH:9]1)=[O:7].[S:36](N)([NH2:39])(=[O:38])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:39][S:36]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[F:20])[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[F:30])([C:21]#[N:22])[CH:10]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[NH:9]1)=[O:7])(=[O:38])=[O:37]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of rac (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-carboxylic acid (3-amino-propyl)-amide (100 mg) in DMF (3 mL), sulfamide (Aldrich, 62 mg) and potassium carbonate (50 mg) were added and the mixture was stirred at 100° C. for 6 hrs. The solvent was removed under reduced pressure and the residue was portioned between EtOAc and water. The organic layer was separated and dried with sodium sulfate. The solvent was removed and the residue was chromatographed on an ISCO machine (70-100% EtOAc/Hexanes) to give a white solid. 25 mg.

Workup

customThe solvent was removed under reduced pressure
customThe organic layer was separated
dry with materialdried with sodium sulfate
customThe solvent was removed
customthe residue was chromatographed on an ISCO machine (70-100% EtOAc/Hexanes)
customto give a white solid

Sources & evidence

ORD record: ord-d73d76bdcb9f4ac7981458aed7d2d017
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354444B2

Reaction notes

Loading…