1,2-Dichloroethane → 5-Methyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623745Notes

Reaction equation

HRID 1623745 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:25][C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)=[O:9]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 130269142-(Benzyloxy)-5-methylbenzoic acid

Product 1

HCID 671071775-Methyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methyl-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 9; 400 mg, 1.65 mmol), 3-pyridinamine (311 mg, 3.30 mmol), HOBT (379 mg, 2.48 mmol) and EDC (475 mg, 2.48 mmol) in DMF (5 ml) was stirred at room temperature overnight. The reaction mixture was poured into water (20 ml), filtered and the solid was washed by water and dried to yield the title compound as a white solid. 220 mg.

Workup

  1. filtrationfiltered
  2. washthe solid was washed by water
  3. customdried

Sources & evidence

ORD record
ord-16f2646870994b789632bccc2074c46d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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