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

HRID 1623769Notes

Reaction equation

HRID 1623769 reaction equation
[CH:1]1[CH:2]=C[C:4]2[N:9](O)N=[N:7][C:5]=2[CH:6]=1.[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:16]([CH:20]=1)[C:17]([OH:19])=O.N1C=CC=C(N)C=1.C(Cl)CCl>CN(C=O)C.O>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:16]([CH:20]=1)[C:17]([NH:7][C:5]1[CH:4]=[N:9][CH:2]=[CH:1][CH:6]=1)=[O:19]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 247719442-(Benzyloxy)-5-hydroxybenzoic acid

Product 1

HCID 513575145-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Solid HOBT (552 mg, 3.60 mmol) was added in one charge to a stirred solution of 5-hydroxy-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 38; 800 mg, 3.28 mmol), 3-pyridinamine (339 mg, 3.60 mmol) and EDC (691 mg, 3.60 mmol) in DMF (30 mL) at room temp. The reaction mixture was stirred at room temperature for 4 h. After 4 h, water was added to the reaction mixture. The reaction mixture was filtered and the residue was washed with ethyl acetate to yield the title compound as a white solid. 500 mg.

Workup

  1. waitAfter 4 h
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-acfc98806e2547aa9496d4aa5e905ee3
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…