1,2-Dichloroethane → N-{3,4-Dioxo-1-phenyl-4-[(2-phenylethyl)amino]butan-2-yl}-2-[3-(4-fluorophenyl)-1H-pyrazol-1-yl]pyridine-3-carboxamide

HRID 1908262Notes

Reaction equation

HRID 1908262 reaction equation
C(Cl)CCl.ClC(Cl)C(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[CH:21][N:20]([C:23]3[N:52]=[CH:51][CH:50]=[CH:49][C:24]=3[C:25]([NH:27][CH:28]([CH:36]([OH:48])[C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:26])[N:19]=2)=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CS(C)=O.[Cl-].[Na+].O>[O:48]=[C:36]([C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:28]([NH:27][C:25]([C:24]1[C:23]([N:20]2[CH:21]=[CH:22][C:18]([C:15]3[CH:14]=[CH:13][C:12]([F:11])=[CH:17][CH:16]=3)=[N:19]2)=[N:52][CH:51]=[CH:50][CH:49]=1)=[O:26])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6597Dichloroacetic AcidHCID 516892Sodium BicarbonateHCID 672384272-(3-(4-Fluorophenyl)-1H-pyrazol-1-yl)-N-(3-hydroxy-4-oxo-4-(phenethylamino)-1-phenylbutan-2-yl)nicotinamide

Product 1

HCID 67238275N-{3,4-Dioxo-1-phenyl-4-[(2-phenylethyl)amino]butan-2-yl}-2-[3-(4-fluorophenyl)-1H-pyrazol-1-yl]pyridine-3-carboxamideYield 48.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

EDC (520 mg, 2.71 mmol) and 2,2-dichloroacetic acid (0.14 ml, 1.69 mmol) were added to a solution of 2-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)-N-(3-hydroxy-4-oxo-4-(phenethylamino)-1-phenylbutan-2-yl)nicotinamide (191 mg, 0.339 mmol) in dimethyl sulfoxide (DMSO) (9 ml), and the reaction mixture was stirred for 45 minutes at room temperature. For work up the reaction mixture was mixed with 100 ml of brine and sat. solution of NaHCO3 (1:1(v/v)) for 10 minutes. The resulting solid was filtered off with suction, washed with water and dried to give 161 mg of the crude product, which was re-crystallized from ethyl acetate to give 92 mg of a white amorphous solid; ESI-MS [M+H]+: 562.3.

Workup

  1. filtrationThe resulting solid was filtered off with suction
  2. washwashed with water
  3. customdried
  4. customto give 161 mg of the crude product, which
  5. customwas re-crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e6c8683922ab4d65906b8bb9e40a132f
Source dataset
uspto-grants-2013_12
Patent number
US08598211B2

Reaction notes

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