Water → HCID 59520400, compound

HRID 1162532Notes

Reaction equation

HRID 1162532 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH2:7].[CH3:13][O:14][C:15](=[O:38])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]=2[C:34](Cl)=[O:35])=[C:19]([Cl:37])[CH:18]=1.O>C1(C)C=CC=CC=1>[CH3:13][O:14][C:15](=[O:38])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]=2[C:34](=[O:35])[NH:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])=[C:19]([Cl:37])[CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1508972-(2,4-Dichlorophenoxy)ethylamineHCID 59520431HCID 59520431, compound

Product 1

HCID 59520400HCID 59520400, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(2,4-Dichloro-phenoxy)-ethylamine 29 (19 mg, 0.09 mmol) in toluene (0.2 mL) is cooled to 0° C. The above solution of intermediate 61 (0.06 mmol) is added and the solution is warmed to room temperature. After stirring at room temperature for 1 hour the mixture is poured into H2O and extracted three times with DCM. The organic layers are combined, dried (MgSO4), filtered, and concentrated to afford crude (3-Chloro-4-{4-[2-(2,4-dichloro-phenoxy)-ethyl-carbamoyl]-3-phenyl-isoxazol-5-yl}-phenyl)-acetic acid methyl ester 62.

Workup

  1. extractionextracted three times with DCM
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-746927f5d9d440ddb7e426e0700cc930
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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