Ethyl 5-amino-2-[2-(diethylamino)ethoxy]benzoate → HCID 59691623, compound

HRID 898635Notes

Reaction equation

HRID 898635 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:29][CH2:30][CH2:31][N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[C:22]([CH:28]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[Cl:1][C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([O:29][CH2:30][CH2:31][N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[C:22]([CH:28]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:8]

Participants

3

Reactant 2

HCID 57632512Ethyl 5-amino-2-[2-(diethylamino)ethoxy]benzoateHCID 59691547(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acid

Product 1

HCID 59691623HCID 59691623, compound

Procedure

Prepared analogously to Example 143 starting from (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (Z2b) and ethyl 5-amino-2-(2-diethylamino-ethoxy)-benzoate. The reaction mixture was evaporated down i. vac. and the residue was dissolved in dichloromethane. The org. phase was washed with water, dried over sodium sulphate and evaporated down i. vac. Purification by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 70:30→50:50) yielded the product.

Workup

  1. customThe reaction mixture was evaporated down i
  2. dissolutionand the residue was dissolved in dichloromethane
  3. washphase was washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated down i
  6. customPurification by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 70:30→50:50)
  7. customyielded the product

Sources & evidence

ORD record
ord-b5c844075f334b5abdfd36757c86564e
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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