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

HRID 1783418
Notes
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Reaction equation

HRID 1783418 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27370014-(Difluoromethoxy)benzyl BromideHCID 866107465-Chloro-pyridine-2-sulfonic acid ((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amide

Product 1

HCID 866107475-Chloro-pyridine-2-sulfonic acid (4-difluoromethoxy-benzyl)-((R)-5.5-difluoro-2-oxo-azepan-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. customthe resultant reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes