Hydrogen Bromide → HCID 44131507, compound

HRID 870326Notes

Reaction equation

HRID 870326 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].[BrH:29]>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].[BrH:29]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 4369359Sitagliptin

Product 1

HCID 44131507HCID 44131507, 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 30 minutes to obtain a clear dissolution. Hydrobromic acid (2.1 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 22 hours. The separated solid is filtered, washed with isopropanol (5 mL), and dried under reduced pressure at about 35° C. for about 1.25 hours to afford the title compound. (Yield: 4.0 g; MC: 2.40% w/w; HPLC purity: 99.70%)

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 35° C. for about 1.25 hours

Sources & evidence

ORD record
ord-20d9631d2f99445f824f39e37f26dd23
Source dataset
uspto-grants-2015_03
Patent number
US08969558B2

Reaction notes

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