Diisopropylethylamine → HCID 53358061, compound

HRID 1500776Notes

Reaction equation

HRID 1500776 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C.C(N(C(C)C)CC)(C)C.[NH:42]1[CH2:47][CH2:46][CH2:45][C@@H:44]([NH:48][C:49]2[CH:54]=[CH:53][N:52]=[C:51]([C:55]3[CH:56]=[N:57][N:58]4[CH:63]=[CH:62][C:61]([C:64]#[N:65])=[CH:60][C:59]=34)[N:50]=2)[CH2:43]1>CN(C=O)C>[F:1][C:2]([F:8])([F:7])[CH2:3][C:4]([N:42]1[CH2:47][CH2:46][CH2:45][C@@H:44]([NH:48][C:49]2[CH:54]=[CH:53][N:52]=[C:51]([C:55]3[CH:56]=[N:57][N:58]4[CH:63]=[CH:62][C:61]([C:64]#[N:65])=[CH:60][C:59]=34)[N:50]=2)[CH2:43]1)=[O:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27779723,3,3-Trifluoropropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67327163HCID 67327163, compound

Product 1

HCID 53358061HCID 53358061, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,3,3-Trifluoropropanoic acid (0.03 mL, 0.29 mmol), N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate (0.12 g, 0.30 mmol) and diisopropylethylamine (0.21 mL, 1.21 mmol) were added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 0.11 g, 0.24 mmol) in N,N′-dimethylformamide (3 mL) and the mixture was stirred at room temperature for 20 hours. The reaction mixture was then partitioned between dichloromethane and 4% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with 4% aqueous sodium hydrogen carbonate solution, dried (MgSO4) and the solvents were evaporated in vacuo. The crude product was purified by flash chromatography (200:1 to 10:1 chloroform/methanol) to give a residue that was repurified by flash chromatography (1:1 hexane/ethyl acetate to 100% ethyl acetate) to give the title compound (0.02 g, 19%) as a pale yellow solid.

Workup

  1. customThe reaction mixture was then partitioned between dichloromethane and 4% aqueous sodium hydrogen carbonate solution
  2. customThe organic layer was separated
  3. washwashed with 4% aqueous sodium hydrogen carbonate solution
  4. dry with materialdried (MgSO4)
  5. customthe solvents were evaporated in vacuo
  6. customThe crude product was purified by flash chromatography (200:1 to 10:1 chloroform/methanol)
  7. customto give a residue that
  8. customwas repurified by flash chromatography (1:1 hexane/ethyl acetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-ab2c8245dcd643799384cdd3969b220a
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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