Fumaric Acid → HCID 57098847, compound

HRID 1416480Notes

Reaction equation

HRID 1416480 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([O:8][CH3:9])[CH2:4][C@H:3]1[O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[N:12]=1.C(O)(=O)/C=C/C(O)=O>C(O)C>[OH:1][C@H:2]1[C@@H:6]([OH:7])[C@H:5]([O:8][CH3:9])[CH2:4][C@@H:3]1[O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[N:12]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 57011354HCID 57011354, compound

Product 1

HCID 57098847HCID 57098847, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[(1R,2R,3S,4S)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline [cf. Example 39] (550 mg) in ethanol (5.5 ml) is added fumaric acid (94 mg), and the mixture is stirred at room temperature for 10 minutes. The precipitated crystals are separated by filtration, and the crystals are recrystallized from water-ethanol to give 4-[(1R,2R,3S,4S)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline 1/2 fumarate (387 mg) as crystals.

Workup

  1. customThe precipitated crystals are separated by filtration
  2. customthe crystals are recrystallized from water-ethanol

Sources & evidence

ORD record
ord-43704eaf404e4d67bac0c12e2191d0b5
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

Loading…