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Fumaric Acid → 2-tert-butyl-4-[(3-methoxypropyl)amino]-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]pyrimidine-5-carboxamide monofumarate

HRID 2192856
Notes
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Reaction equation

HRID 2192856 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])[CH2:23][NH:22][CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42]>C(OCC)(=O)C.CO>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42].[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])[CH2:23][NH:22][CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:3])([CH3:4])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 252424382-~{tert}-Butyl-4-(3-Methoxypropylamino)-~{n}-(2-Methylpropyl)-~{n}-[(3~{s},5~{r})-5-Morpholin-4-Ylcarbonylpiperidin-3-Yl]pyrimidine-5-Carboxamide

Product 1

HCID 866492982-tert-butyl-4-[(3-methoxypropyl)amino]-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]pyrimidine-5-carboxamide monofumarateYield 65.1%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2-tert-Butyl-4-[(3-methoxypropyl)amino]-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]pyrimidine-5-carboxamide (5.22 g) was dissolved in ethyl acetate (80 ml), and a solution of fumaric acid (1.17 g) in methanol (20 ml) was added. The mixture was heated to 70° C., stirred well and filtered. The filtrate was concentrated under reduced pressure, and the obtained white solid (6.40 g) was suspended in ethyl acetate (190 ml), and dissolved by heating to 70° C. Acetonitrile (190 ml) heated to 70° C. was added, and the mixture was allowed to cool to 50° C. Seed crystals (10 mg) were added, and the mixture was allowed to cool to room temperature with stirring. The mixture was further stirred at 0° C. for 2 hr, and the precipitated white solid was collected by filtration, and washed with ethyl acetate-acetonitrile (1:1). The obtained white crystals were dried under reduced pressure at 100° C. for 12 hr to give the object compound (4.16 g).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutiondissolved
  4. temperatureby heating to 70° C
  5. temperatureAcetonitrile (190 ml) heated to 70° C.
  6. additionwas added
  7. temperatureto cool to 50° C
  8. additionSeed crystals (10 mg) were added
  9. temperatureto cool to room temperature
  10. stirringwith stirring
  11. stirringThe mixture was further stirred at 0° C. for 2 hr
  12. filtrationthe precipitated white solid was collected by filtration
  13. washwashed with ethyl acetate-acetonitrile (1:1)
  14. customThe obtained white crystals were dried under reduced pressure at 100° C. for 12 hr

Sources & evidence

ORD record
ord-125a988a6e4649df875e8498b8880c31
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329691B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes