3-Amino-4-hydroxybenzohydrazide → (R)-2-{4-[(3-Amino-4-hydroxybenzoyl)hydrazonomethyl]-3-methoxyphenoxy}-N-(1-benzylpyrrolidin-3-yl)acetamide

HRID 1166780Notes

Reaction equation

HRID 1166780 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][NH2:8])=[O:6].[CH2:13]([N:20]1[CH2:24][CH2:23][C@@H:22]([NH:25][C:26](=[O:39])[CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([CH:35]=O)=[C:31]([O:37][CH3:38])[CH:30]=2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][N:8]=[CH:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:27][C:26]([NH:25][C@@H:22]2[CH2:23][CH2:24][N:20]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:21]2)=[O:39])=[CH:30][C:31]=1[O:37][CH3:38])=[O:6]

Participants

4

Reactant 2

HCID 5858793-Amino-4-hydroxybenzohydrazideHCID 54022232(R)-N-(1-benzylpyrrolidin-3-yl)-2-(4-formyl-3-methoxyphenoxy)acetamide

Product 1

HCID 70026806(R)-2-{4-[(3-Amino-4-hydroxybenzoyl)hydrazonomethyl]-3-methoxyphenoxy}-N-(1-benzylpyrrolidin-3-yl)acetamideYield 70.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The above 3-amino-4-hydroxybenzoic acid hydrazide (50 mg, 0.3 mmol) and the above (R)-N-(1-benzylpyrrolidin-3-yl)-2-(4-formyl-3-methoxyphenoxy)acetamide (110 mg, 0.3 mmol) were dissolved in 2-propanol (4 ml) and the mixture was heated at reflux temperature for 16 hours. The cooled mixture was filtered and the precipitate was washed with 2-propanol (2×3 ml) and dried by suction to afford 109 mg (70%) of the title compound as a solid. M.p.: 157-160° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. filtrationThe cooled mixture was filtered
  4. washthe precipitate was washed with 2-propanol (2×3 ml)
  5. customdried by suction

Sources & evidence

ORD record
ord-a5538ba0f6434e799a68fb65e142e202
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

Loading…