Diisopropylethylamine → HCID 89618449, compound

HRID 926699Notes

Reaction equation

HRID 926699 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[CH:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]1[CH:28]=[CH:27][N:26]2[N:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[C:25]2[CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:59]1[CH2:63][CH2:62][C@H:61]([OH:64])[CH2:60]1>CN(C=O)C.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[CH:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]1[CH:28]=[CH:27][N:26]2[N:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[C:25]2[CH:24]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[CH:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]1[CH:28]=[CH:27][N:26]2[N:29]=[CH:30][C:31]([C:32]([N:59]3[CH2:63][CH2:62][C@H:61]([OH:64])[CH2:60]3)=[O:34])=[C:25]2[CH:24]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89618449HCID 89618449, compound

Product 2

HCID 71580990HCID 71580990, compoundHCID 89618449HCID 89618449, compoundYield 200%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (100 mg, 0.29 mmol) was prepared by the method mentioned in Example-3. DIPEA (93.6 mg, 0.72 mmol) was added to a stirred solution of 5-(2-(2,5-difluorophenyl) pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (100 mg, 0.29 mmol) in DMF (1.5 mL) followed by addition of HATU (165 mg, 0.437 mmol) to the reaction mixture. After 2 minutes of stirring, (S)-pyrrolidin-3-ol (81.8 mg, 0.43 mmol) was added and the resulting mixture was stirred at 20-35° C. for 2 h. The reaction mixture was diluted with cold water; extracted with ethyl acetate; dried over sodium sulfate; and concentrated under reduced pressure to get a residue. The residue thus obtained was purified by column chromatography (60-120 silica gel and 3% EtOAc in Hexane as eluent) to afford (5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridin-3-yl)((S)-3-hydroxypyrrolidin-1-yl)methanone

Workup

  1. stirringthe resulting mixture was stirred at 20-35° C. for 2 h
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationand concentrated under reduced pressure
  5. customto get a residue
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (60-120 silica gel and 3% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-cf53e354bb75450491f0159deeb57217
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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