Potassium Carbonate → 5-Chloro-pyridine-2-sulfonic acid (4-difluoromethoxy-benzyl)-((R)-5.5-difluoro-2-oxo-azepan-3-yl)-amide

HRID 1783418Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

5-Chloro-pyridine-2-sulfonic acid ((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amide (0.21 g, 0.61 mmol), 4-(difluoromethoxy)benzyl bromide (0.23 g, 0.91 mmol), K2CO3 (0.85 g, 6.08 mmol), KI (0.02 g, 0.12 mmol) were added to dry DMF (10 ml) and the resultant reaction mixture was stirred for 1.5 h at 65° C. and for additional 3 h at room temperature under an argon atmosphere. The solvent was removed under reduced pressure and the residue was purified over silica gel (first: ethyl acetate/n-heptane 1:2 v/v; second: dichloromethane/MeOH, 100:0-95:5): brownish oil, 0.23 g;

Workup

customthe resultant reaction mixture
customThe solvent was removed under reduced pressure
customthe residue was purified over silica gel (first: ethyl acetate/n-heptane 1:2 v/v; second: dichloromethane/MeOH, 100:0-95:5)

Sources & evidence

ORD record: ord-6873cfde16ff470a95b2f71e5fbab44a
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501406B2

Reaction notes

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