Fumaric Acid → 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran fumarate

HRID 1291055Notes

Reaction equation

HRID 1291055 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][N:26]=[C:25]3[CH3:29])=[CH:20][CH:19]=2)[CH:5]=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>CO>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[F:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][N:26]=[C:25]3[CH3:29])=[CH:20][CH:19]=2)[CH:5]=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 103860554-(5-fluoro-3-(4-(2-methyl-1H-imidazol-1-yl)benzyloxy)phenyl)-4-methoxy-3,4,5,6-tetrahydro-2H-pyran

Product 1

HCID 189201814-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran fumarateYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran (150 mg, 0.38 mmol) in MeOH (3 ml) was added fumaric acid (44 mg, 0.38 mmol). The resulting solution was concentrated in vacuo. The residual solid was recrystallized from ethanol to afford 152 mg (77%) of 4-[5-fluoro-3-[4-(2-methylimidazol- 1-yl)benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran fumarate as a white powder.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customThe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-d8e6d36c431046c3866d8772099d9df7
Source dataset
uspto-grants-1998_05
Patent number
US05753682

Reaction notes

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