HCID 71724478, compound → Sitagliptin

HRID 1928529Notes

Reaction equation

HRID 1928529 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].S([O-])([O-])(=O)=O>C(#N)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]

Participants

3

Reactant 1

HCID 71724478HCID 71724478, compound3×

Product 1

HCID 4369359Sitagliptin

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As used herein, Sitagliptin sulfate Form S2 refers to a crystalline Sitagliptin sulfate characterized by a powder XRD pattern with peaks at 9.3°, 9.7°, 15.2°, 15.6°, and 25.4°±0.2° 2θ. Sitagliptin sulfate Form S2 can be obtained, for example, by forming a solution of Sitagliptin base in acetonitrile; combining the solution with sulfuric acid to form a precipitate; and isolating the obtained precipitate; wherein, the sulfuric acid is used at a mol ratio of about 1:0.5 of Sitagliptin base to sulfuric acid, e.g., as indicated in PCT application No. PCT/US10/29098.

Workup

  1. customcharacterized by a powder XRD pattern with peaks at 9.3°, 9.7°, 15.2°, 15.6°
  2. custom25.4°±0.2° 2θ

Sources & evidence

ORD record
ord-219659e264034e649e4924f18a259de2
Source dataset
uspto-grants-2012_05
Patent number
US08183373B2

Reaction notes

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