1,2-Dichloroethane → N-{1-[Amino(oxo)acetyl]pentyl}-2-(4-phenyl-1H-pyrazol-1-yl)nicotinamide

HRID 2280959Notes

Reaction equation

HRID 2280959 reaction equation
C(Cl)CCl.ClC(Cl)C(O)=O.[NH2:11][C:12](=[O:40])[CH:13]([CH:15]([NH:20][C:21]([C:23]1[C:24]([N:29]2[CH:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:31]=[N:30]2)=[N:25][CH:26]=[CH:27][CH:28]=1)=[O:22])[CH2:16][CH2:17][CH2:18][CH3:19])[OH:14].O>CS(C)=O>[NH2:11][C:12](=[O:40])[C:13]([CH:15]([NH:20][C:21](=[O:22])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[N:29]1[CH:33]=[C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:31]=[N:30]1)[CH2:16][CH2:17][CH2:18][CH3:19])=[O:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 6597Dichloroacetic AcidHCID 66720115N-[1-(2-amino-1-hydroxy-2-oxoethyl)pentyl]-2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxamide

Product 1

HCID 25157359N-{1-[Amino(oxo)acetyl]pentyl}-2-(4-phenyl-1H-pyrazol-1-yl)nicotinamideYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.47 g of EDC and 0.08 ml of dichloroacetic acid were added to 100 mg of N-[1-(2-amino-1-hydroxy-2-oxoethyl)pentyl]-2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxamide (0.25 mmol) in 4 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature overnight. For workup, the reaction mixture was poured into H2O, and the resulting precipitate was filtered off with suction and dried in a vacuum drying oven at 40° C. 77 mg of the title compound were obtained as an amorphous white solid. ESI-MS [M+H]+=406.2

Workup

  1. filtrationthe resulting precipitate was filtered off with suction
  2. customdried in a vacuum
  3. customdrying oven at 40° C

Sources & evidence

ORD record
ord-1943ae03fa8b4f1ba691cddb2e018f6f
Source dataset
uspto-grants-2015_09
Patent number
US09139557B2

Reaction notes

Loading…