1,2-Dichloroethane → N-(1H-Pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

HRID 624048Notes

Reaction equation

HRID 624048 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([OH:14])=O)[CH:2]=1.C1C=C[C:19]2[N:24](O)[N:23]=[N:22][C:20]=2[CH:21]=1.C(Cl)CCl.N1C=C(N)C=N1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[NH:23]1[CH:21]=[C:20]([NH:22][C:12]([C:8]2[N:9]=[CH:10][O:11][C:7]=2[C:3]2[CH:2]=[C:1]([CH3:15])[CH:6]=[CH:5][CH:4]=2)=[O:14])[CH:19]=[N:24]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 780351H-pyrazol-4-amineHCID 81531DiisopropylethylamineHCID 299230925-(m-Tolyl)oxazole-4-carboxylic acid

Product 1

HCID 68283740N-(1H-Pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (11.18 g) in DCM (65 mL), HOBT (11.15 g, 0.083 mol) and EDC (15.8 g, 0.083 mol) was added at 0° C. This suspension was stirred at this temperature for 10 min, then it was added to a suspension was of 1H-pyrazol-4-amine (5.48 g) and DIPEA (17.65 mL) in DCM (50 mL). The resulting mixture was allowed to warm to rt and was stirred at rt for 18 h. Percipitation of the desired compound was obtained by the addition of water. The solid was filtered and dried to yield the title compound. LC-MS conditions B: tR=0.63 min, [M+H]+=269.13.

Workup

  1. additionit was added to a suspension
  2. stirringwas stirred at rt for 18 h

Sources & evidence

ORD record
ord-8a558551a3c84f9bb3688e4d7ee08375
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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