1-Hydroxybenzotriazole → HCID 58755345, compound

HRID 2251324Notes

Reaction equation

HRID 2251324 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])=[N:13][O:14][C:15]=2[CH:16]([CH3:18])[CH3:17])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:27]([O:38][CH3:39])(=[O:37])[C:28]1[CH:36]=[CH:35][C:31]([C:32]([O-])=[O:33])=[CH:30][CH:29]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])=[N:13][O:14][C:15]=2[CH:16]([CH3:18])[CH3:17])[CH:6]=[CH:5][C:3]=1[NH:4][C:32]([C:31]1[CH:35]=[CH:36][C:28]([C:27]([O:38][CH3:39])=[O:37])=[CH:29][CH:30]=1)=[O:33]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 36144541,4-Benzenedicarboxylic acid, methyl esterHCID 24757446HCID 24757446, compound

Product 1

HCID 58755345HCID 58755345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}aniline (85 mg, 206 μmol), monomethyl terephthalate (37.2 mg, 206 μmol), 1-hydroxybenzotriazole (5.6 mg, 41 μmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (39.6 mg, 206 μmol) in dichloromethane (1 mL) was stirred at ambient temperature for 24 h. The reaction was partitioned with ethyl acetate and water. The organic layer was washed sequentially with saturated aqueous sodium hydrogensulfate and brine, then was dried over anhydrous sodium sulfate, filtered, and condensed to a residue which was chromatographed on silica gel eluting with 30% ethyl acetate/hexanes. Yield=65 mg, (55%) of methyl 4-{[(2-chloro-4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}phenyl)amino]carbonyl}-benzoate.

Workup

  1. customThe reaction was partitioned with ethyl acetate and water
  2. washThe organic layer was washed sequentially with saturated aqueous sodium hydrogensulfate and brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customcondensed to a residue which
  6. customwas chromatographed on silica gel eluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-95fb8ab711734c9eb7de07fbf4f83c62
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

Loading…