Picolinic acid → HCID 86597660, compound

HRID 350750Notes

Reaction equation

HRID 350750 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][P:26]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=2)=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40](O)=[O:41].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([NH:1][C:40]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=3)=[O:41])[S:3][C:4]=2[CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][P:26]([O:28][CH2:29][CH3:30])([O:31][CH2:32][CH3:33])=[O:27])=[CH:21][CH:20]=2)=[O:17])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86597659HCID 86597659, compound

Product 1

HCID 86597660HCID 86597660, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]-N-[4-(diethylphosphonomethyl)phenyl]propionamide (500 mg), pyridine-2-carboxylic acid (145 mg), 1-hydroxybenzotriazole (180 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (225 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 24 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to give 3-{4-(4-chlorophenyl)-2-[(2-pyridinylcarbonyl)amino)-5-thiazolyl}-N-[4-(diethylphosphonomethyl)phenyl]propionamide was obtained as crystals (560 mg). Recrystallization from ethyl acetate gave colorless prism crystals (350 mg, yield: 58%). melting point: 184–185° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-186ee6501ba446ee9c76e9c53b7495ae
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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