Maleic Acid → HCID 10025539, compound

HRID 1196909Notes

Reaction equation

HRID 1196909 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28]>CCOCC>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28].[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 10025540HCID 10025540, compound

Product 1

HCID 10025539HCID 10025539, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The free base of Example 43 was dissolved in ether (5 mL) with stirring. A saturated solution of maleic acid in ether (10 mL) was added. The white precipitate was filtered and washed with copious amounts of ether. Drying in vacuo afforded a white powder (521 mg):mp 132°-134° C.; 1H-NMR (DMSO-d6):7.5(s,5H), 7.3-7.1(m,4H), 6.05(s,2H), 4.3(s,2H), 3.95(s,2H), 3.6-2.7(m,10H), 2.15-1.5(m,4H); Anal.:Calcd for C20H22FNO-C4H4O4 -0.75 H2O:C,65.36, H,6.29, N,3.18; Found:C,65.53, 65.60, M,5.93, 5.90, N,3.20, 3.21.

Workup

  1. filtrationThe white precipitate was filtered
  2. washwashed with copious amounts of ether
  3. customDrying in vacuo

Sources & evidence

ORD record
ord-44399209a8b04095bcc8f44751ef1db6
Source dataset
uspto-grants-1992_05
Patent number
US05116846

Reaction notes

Loading…