Cyclopropanesulfonamide → HCID 68172329, compound

HRID 2408079Notes

Reaction equation

HRID 2408079 reaction equation
[CH3:1][C:2]1([CH3:27])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](O)=[O:13])[CH:10]=2)[NH:5][CH:4]([C:15]2[CH:16]=[N:17][CH:18]=[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:20]=2)[CH2:3]1.[CH:28]1([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:30][CH2:29]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1([CH3:27])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([NH:34][S:31]([CH:28]3[CH2:30][CH2:29]3)(=[O:33])=[O:32])=[O:13])[CH:10]=2)[NH:5][CH:4]([C:15]2[CH:16]=[N:17][CH:18]=[C:19]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[CH:20]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 15765418CyclopropanesulfonamideHCID 70496357HCID 70496357, compound

Product 1

HCID 68172329HCID 68172329, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,4-dimethyl-2-(5-morpholin-4-yl-pyridin-3-yl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (200 mg, 0.54 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (160 mg, 0.82 mmol), 4-dimethylaminopyridine (100 mg, 0.82 mmol), cyclopropane sulfonic acid amide (196 mg, 1.62 mmol) in dichloromethane (10 mL) was refluxed for 12 h. Removal of the solvent to afford the oil residue. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded cyclopropanesulfonic acid [4,4-dimethyl-2-(5-morpholin-4-yl-pyridin-3-yl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (38 mg, 15%) as a light yellow solid: MS (ESI) M+1=471.2.

Workup

  1. temperaturewas refluxed for 12 h
  2. customRemoval of the solvent
  3. customto afford the oil residue
  4. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water)

Sources & evidence

ORD record
ord-2a54c8759b9f4904a95d376bb794586f
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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