Water → HCID 10180362, compound
Reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C([N:9](CC)CC)C.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.[C:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36](Cl)(=[O:38])=[O:37])(OCC)=[O:26].[OH2:40]>CN(C)C1C=CN=CC=1.C(#N)C>[OH:40][NH:9][C:25](=[O:26])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[CH2:3]1)(=[O:38])=[O:37]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Part A: 3-aminopyrrolidine (636 mg, 4 mmol), triethylamine (2.7 mL, 20 mmol), and 4-(dimethylamino)pyridine (75 mg) were suspended in acetonitrile. After 10 min, the reaction was chilled to 0° C. 4-methoxybenzoyl chloride (0.54 mL, 4 mmol) was added drop-wise. After 30 min, 2-carboethoxybenzenesulfonyl chloride (0.996 g, 4.0 mmol) was introduced drop-wise by syringe. The mixture was stirred at 0° C. for 1 hr, and then at ambient temperature for 2 hr. Water was added (50 mL). The mixture was extracted using ethyl acetate (2×50 mL). The organic layer was dried over MgSO4, filtered through silica, and concentrated. The residue was purified using silica gel chromatography using 1:1 ethyl acetate:hexane to ethyl acetate as eluant. The desired amide sulfonamide was isolated as a foam (282 mg, 16%).
Workup
- waitAfter 30 min
- waitat ambient temperature for 2 hr
- extractionThe mixture was extracted
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered through silica
- concentrationconcentrated
- customThe residue was purified
Sources & evidence
- ORD record
- ord-53c6fbfbf5de47ecb47eb30c4e9dd80e
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696449B2
Reaction notes
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