Water → HCID 131731755, compound

HRID 2403628Notes

Reaction equation

HRID 2403628 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([C:32](=[O:35])[CH2:33][NH2:34])[CH3:31])[CH:24]=3)=[CH:19][N:18]=2)[CH2:13][CH2:12]1)[C:5]([OH:7])=[O:6].O.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>C1COCC1>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([C:32](=[O:35])[CH2:33][NH2:34])[CH3:31])[CH:24]=3)=[CH:21][N:22]=2)[CH2:13][CH2:12]1)[C:5]([OH:7])=[O:6].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([CH3:31])[C:32](=[O:35])[CH2:33][NH2:34])[CH:24]=3)=[CH:21][N:22]=2)[CH2:13][CH2:12]1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 444972Fumaric AcidHCID 51036303HCID 51036303, compound

Product 1

HCID 131731755HCID 131731755, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Next, 3-chloro-4-{4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}benzoic acid (2 g) was suspended in THF (40 ml)-H2O (40 ml), and fumaric acid (938 mg) was added thereto, followed by stirring at 90° C. for 1 hour. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. To the residue was added THF (20 ml)-H2O (20 ml), followed by stirring at 90° C. for 1 hour as it was suspended. The mixture was cooled to room temperature, followed by stirring overnight. After the mixture was filtered, washed with THF—H2O (1:1), and then dried at 50° C. for 5 hours under reduced pressure to obtain 3-chloro-4-{4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}benzoic acid hemifumarate (1.7 g) as a colorless crystal.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the residue was added THF (20 ml)-H2O (20 ml)
  5. stirringby stirring at 90° C. for 1 hour as it
  6. temperatureThe mixture was cooled to room temperature
  7. stirringby stirring overnight
  8. filtrationAfter the mixture was filtered
  9. washwashed with THF—H2O (1:1)
  10. customdried at 50° C. for 5 hours under reduced pressure

Sources & evidence

ORD record
ord-bc85fe7fb4c84c76ad434be55cd99939
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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