HCID 178464552, compound → HCID 178457524, compound

HRID 1770203Notes

Reaction equation

HRID 1770203 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:14](=[NH:24])[NH:15][CH:16]([CH3:23])[C:17]1C=CC=CC=1>CC(N)C>[OH:1][C:2]1[C:7]([CH2:8][C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:14](=[NH:24])[NH:15][CH:16]([CH3:17])[CH3:23]

Participants

3

Reactant 1

HCID 178464552HCID 178464552, compound

Product 1

HCID 178457524HCID 178457524, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6363IsopropylamineSolvent

Conditions

Temperature
80 °C

Procedure

5 g (0.0156 mole) of 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-N-α-methylbenzyl-benzenecarboximidamide prepared in 1.a) above and 50 ml of 2-propanamine are placed in a digester and are heated at 80° C. for 54 hours, then at 100° C. for 46 hours. The solvent is evaporated and the residue is purified by preparative liquid chromatography (silica: 600 g; eluent: 89:10:1 (v/v/v) mixture of dichloromethane-methanol-ammonia). After evaporation of the solvents, 3.6 g of a pale yellow solid product are obtained which are recrystallized twice from acetonitrile. 1.25 g of 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-N-(1-methylethyl)-benzenecarboximidamide are obtained. Yield: 31%.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is purified by preparative liquid chromatography (silica: 600 g; eluent: 89:10:1 (v/v/v) mixture of dichloromethane-methanol-ammonia)
  3. customAfter evaporation of the solvents, 3.6 g of a pale yellow solid product
  4. customare obtained which
  5. customare recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-42fd6c8aabef45a284e8e8cd750ba365
Source dataset
uspto-grants-1995_01
Patent number
US05385927

Reaction notes

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