1,2-Dichloroethane → 2-(4-tert-Butylphenyl)-N-{3-fluoro-4-[(methylsulfonyl)amino]benzyl}cyclopropanecarboxamide

HRID 607496Notes

Reaction equation

HRID 607496 reaction equation
CN(C=O)C.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[CH2:18][C@H:17]2[C:19]([OH:21])=O)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(Cl)CCl.Cl.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[C:31]([F:40])[CH:30]=1>CN(C1C=CN=CC=1)C.C(N(CC)CC)C>[C:6]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:18][CH:17]2[C:19]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[C:31]([F:40])[CH:30]=2)=[O:21])=[CH:14][CH:15]=1)([CH3:7])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 841882Cyclopropanecarboxylic acid, 2-[4-(1,1-dimethylethyl)phenyl]-, trans-HCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride

Product 1

HCID 118538692-(4-tert-Butylphenyl)-N-{3-fluoro-4-[(methylsulfonyl)amino]benzyl}cyclopropanecarboxamideYield 9.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To a DMF (10 ml) solution of trans-2-(4-tert-butylphenyl)cyclopropanecarboxylic acid (435 mg, 1.89 mmol)) [Journal of medicinal chemistry, 2005, vol. 48, 71-90], EDC (572 mg, 3.0 mmol), DMAP (73 mg, 0.6 mmol), triethylamine (0.836 ml) and N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride (507 mg, 1.89 mmol) were added and the mixture was stirred for 5 hours at room temperature. Then, the reaction was quenched with saturated sodium bicarbonate aqueous solution and the whole was extracted with EtOAc/hexane (3:1), and dried over sodium sulfate. Then, filtration, evaporation, and purification by silica gel column chromatography, eluting with hexane/EtOAc (1:2), gave title compound (75 mg, 9% yield) as white solids.

Workup

  1. customThen, the reaction was quenched with saturated sodium bicarbonate aqueous solution
  2. extractionthe whole was extracted with EtOAc/hexane (3:1)
  3. dry with materialdried over sodium sulfate
  4. filtrationThen, filtration, evaporation, and purification by silica gel column chromatography
  5. washeluting with hexane/EtOAc (1:2)

Sources & evidence

ORD record
ord-b3ea533fd8ed417a8f050adabdfc3e1b
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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