Water → HCID 59520429, compound

HRID 1162517Notes

Reaction equation

HRID 1162517 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:33])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:27]([C:28](Cl)=[O:29])=[C:26]([CH3:31])[O:25][N:24]=2)=[C:19]([Cl:32])[CH:18]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.CC#N>[CH3:13][O:14][C:15](=[O:33])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:27]([C:28](=[O:29])[NH:7][CH2:6][CH2:5][O:4][C:3]3[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=3[Cl:1])=[C:26]([CH3:31])[O:25][N:24]=2)=[C:19]([Cl:32])[CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1508972-(2,4-Dichlorophenoxy)ethylamineHCID 59520424HCID 59520424, compound

Product 1

HCID 59520429HCID 59520429, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(2,4-Dichloro-phenoxy)-ethylamine 29 (17 mg, 0.08 mmol) in toluene (2 mL) is cooled to 0° C. A solution of intermediate 26 (0.08 mmol) and triethylamine (23 μL, 0.16 mmol) in MeCN (1 mL) is added and the solution is warmed to room temperature. After stirring at room temperature for 1 h the mixture is poured into H2O and extracted three times with EtOAc. The organic layers are combined, dried (MgSO4), filtered, and concentrated to afford crude (3-Chloro-4-{4-[2-(2,4-dichloro-phenoxy)-ethylcarbamoyl]-5-methyl-isoxazol-3-yl}-phenyl)-acetic acid methyl ester 30.

Workup

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

Sources & evidence

ORD record
ord-f4cc71de5f154dccbefd3921e4a5197b
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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