Water → HCID 10180362, compound

HRID 1241889Notes

Reaction equation

HRID 1241889 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

8

Reactant 5

HCID 962WaterHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 1644013-AminopyrrolidineHCID 3763467Benzoic acid, 2-(chlorosulfonyl)-, ethyl ester (9CI)

Product 1

HCID 10180362HCID 10180362, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

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 minutes, the reaction was chilled to zero degrees Celsius. 4-Methoxybenzoyl chloride (0.54 mL, 4 mmol) was added, drop-wise. After 30 minutes, 2-carboethoxybenzenesulfonyl chloride (0.996 g, 4.0 mmol) was introduced, drop-wise, by syringe. The mixture was stirred at zero Celsius for 1 hour, then at ambient temperature for 2 hours. Water was added (50 mL). The mixture was extracted using ethyl acetate (2×50 mL). The organic layer was dried over magnesium sulfate, 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

  1. temperaturethe reaction was chilled to zero degrees Celsius
  2. waitAfter 30 minutes
  3. customdrop-wise, by syringe
  4. waitat ambient temperature for 2 hours
  5. extractionThe mixture was extracted
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered through silica
  8. concentrationconcentrated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-c585aa3b650544b6a6ca3e7e0c9a77a9
Source dataset
uspto-grants-2006_10
Patent number
US07115632B1

Reaction notes

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