Fumaric Acid → HCID 86647030, compound

HRID 870332Notes

Reaction equation

HRID 870332 reaction equation
[CH:1]1[C:2]([CH2:10][C@@H:11]([NH2:28])[CH2:12][C:13]([N:15]2[CH2:27][C:19]3=[N:20][N:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[N:18]3[CH2:17][CH2:16]2)=[O:14])=[C:3]([F:9])[CH:4]=[C:5]([F:8])[C:6]=1[F:7].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>C(O)(C)C>[CH:1]1[C:2]([CH2:10][C@@H:11]([NH2:28])[CH2:12][C:13]([N:15]2[CH2:27][C:19]3=[N:20][N:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[N:18]3[CH2:17][CH2:16]2)=[O:14])=[C:3]([F:9])[CH:4]=[C:5]([F:8])[C:6]=1[F:7].[C:29]([O-:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([O-:34])=[O:33]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 4369359Sitagliptin

Product 1

HCID 86647030HCID 86647030, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Sitagliptin (4 g) and isopropanol (60 mL) are charged into a round-bottom flask and the mixture is heated to about 80° C. for about 30 minutes to obtain a clear dissolution. Fumaric acid (1.14 g) is added and the reaction mixture is refluxed for about 2 hours. The reaction mixture is cooled to about 30° C. and stirred for about 21 hours. The separated solid is filtered, washed with isopropanol (4 mL), and dried under reduced pressure at about 45° C. for about 2 hours to afford the title compound. (Yield: 4.0 g; MC: 1.05% w/w; HPLC purity: 99.47%)

Workup

  1. customto obtain
  2. dissolutiona clear dissolution
  3. temperaturethe reaction mixture is refluxed for about 2 hours
  4. temperatureThe reaction mixture is cooled to about 30° C.
  5. filtrationThe separated solid is filtered
  6. washwashed with isopropanol (4 mL)
  7. customdried under reduced pressure at about 45° C. for about 2 hours

Sources & evidence

ORD record
ord-2f1f9016a78e40da90a1c3e617a3a0f5
Source dataset
uspto-grants-2015_03
Patent number
US08969558B2

Reaction notes

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