4-(2-Dimethylamino-ethoxy)-benzoic acid → HCID 19424255, compound

HRID 2259215Notes

Reaction equation

HRID 2259215 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:25]=[C:24]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[S:23][C:22]=2[CH:31]=1>>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]2[C:25]([C:10]([C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:15])=[CH:14][CH:13]=3)=[O:12])=[C:24]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[S:23][C:22]=2[CH:31]=1

Participants

3

Reactant 2

HCID 64866194-(2-Dimethylamino-ethoxy)-benzoic acidHCID 19002796HCID 19002796, compound

Product 1

HCID 19424255HCID 19424255, compoundYield 42.7%

Procedure

The same operations as in Preparation example 6 were carried out using 200 mg of 4-[2-(dimethylamino)ethoxy]benzoic acid in place of 4-(2-chloroethoxy)benzoic acid and 45 mg of 6-methoxy-2-cyclopentylbenzo[b]thiophene in place of 6-methoxy-2-cyclohexylbenzo[b]thiophene, and then purification was carried out by TLC (developing solvent, chloroform:methanol=19:1) to obtain 35 mg of (6-methoxy-2-cyclopentylbenzo[b]thien-3-yl)[4-[2-(dimethylamino)ethoxy]phenyl]methanone.

Workup

  1. customThe same operations as in Preparation example 6
  2. custompurification

Sources & evidence

ORD record
ord-735b7fcec5444f868b64cc438158fc18
Source dataset
uspto-grants-1995_12
Patent number
US05472962

Reaction notes

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