Trifluoroacetic acid → HCID 86685339, compound

HRID 1853082Notes

Reaction equation

HRID 1853082 reaction equation
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[C:18]([C:20]3[N:25]4[CH:26]=[CH:27][N:28]=[C:24]4[CH:23]=[C:22]([C:29]4[CH:30]=[N:31][N:32]([CH:34]5[CH2:37][O:36][CH2:35]5)[CH:33]=4)[N:21]=3)[CH:17]=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl.C1(C)C=CC=CC=1>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[O:36]1[CH2:37][CH:34]([N:32]2[CH:33]=[C:29]([C:22]3[N:21]=[C:20]([C:18]4[CH:17]=[N:16][N:15]([C:4]5([CH2:3][C:1]#[N:2])[CH2:7][NH:6][CH2:5]5)[CH:19]=4)[N:25]4[CH:26]=[CH:27][N:28]=[C:24]4[CH:23]=3)[CH:30]=[N:31]2)[CH2:35]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86685340HCID 86685340, compound

Product 1

HCID 86685339HCID 86685339, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(cyanomethyl)-3-(4-(7-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (0.75 g, 1.5 mmol) was suspended in DCM (15 mL) and TFA (5 mL) and stirred at ambient temperature for 2 hours. The reaction mixture was diluted with toluene and concentrated under reduced pressure. The material was transferred to another flask with DCM and MeOH and concentrated under reduced pressure to afford the crude 2-(3-(4-(7-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile bis(2,2,2-trifluoroacetate) (1.31 g, 1.46 mmol, 97.4% yield), which was used in the next step without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe material was transferred to another flask with DCM and MeOH
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37d63e4ff6e74ae3b300afc8d173e215
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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