Benzoic Acid → HCID 86647027, compound

HRID 870328Notes

Reaction equation

HRID 870328 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:37])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>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-:37])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 4369359Sitagliptin

Product 1

HCID 86647027HCID 86647027, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Sitagliptin (5 g) and isopropanol (75 mL) are charged into a round-bottom flask and the mixture is heated to about 80° C. for about 20 minutes to obtain a clear dissolution. Benzoic acid (1.49 g) is added and the reaction mixture is refluxed for about 1.5 hours. The reaction mixture is cooled to about 30° C. and stirred for about 21.5 hours. The separated solid is filtered, washed with isopropanol (5 mL), and dried under reduced pressure at about 40° C. for about 1.5 hours to afford the title compound. (Yield: 5.9 g; MC: 0.80% w/w; HPLC purity: 99.82%)

Workup

  1. customto obtain
  2. dissolutiona clear dissolution
  3. temperaturethe reaction mixture is refluxed for about 1.5 hours
  4. temperatureThe reaction mixture is cooled to about 30° C.
  5. filtrationThe separated solid is filtered
  6. washwashed with isopropanol (5 mL)
  7. customdried under reduced pressure at about 40° C. for about 1.5 hours

Sources & evidence

ORD record
ord-64827364e8384b4d82c26d4c939f529f
Source dataset
uspto-grants-2015_03
Patent number
US08969558B2

Reaction notes

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