Trifluoroacetic acid → HCID 67458185, compound

HRID 1853054Notes

Reaction equation

HRID 1853054 reaction equation
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[CH:18][C:17]([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]([CH3:34])[CH:33]=4)[N:21]=3)=[CH:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>C(Cl)Cl>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[CH3:34][N:32]1[CH:33]=[C:29]([C:22]2[N:21]=[C:20]([C:17]3[CH:18]=[CH:19][N:15]([C:4]4([CH2:3][C:1]#[N:2])[CH2:7][NH:6][CH2:5]4)[CH:16]=3)[N:25]3[CH:26]=[CH:27][N:28]=[C:24]3[CH:23]=2)[CH:30]=[N:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71256555HCID 71256555, compound

Product 1

HCID 67458185HCID 67458185, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(cyanomethyl)-3-(3-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrrol-1-yl)azetidine-1-carboxylate (Preparation O, 79.0 mg, 0.172 mmol) in dry DCM (1.5 mL) was added trifluoroacetic acid (2 mL) and the mixture stirred at ambient temperature for 3 hours. The mixture was concentrated and the residual gel was treated with EtOAc and sonicated until a white suspension. The EtOAc was decanted, the residual solid was washed with EtOAc and dried in vacuum to afford the title compound (trifluoroacetate salt, 100 mg, 99% yield) as an ivory white solid. MS (apci) m/z=359.2.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residual gel was treated with EtOAc
  3. customsonicated until a white suspension
  4. customThe EtOAc was decanted
  5. washthe residual solid was washed with EtOAc
  6. customdried in vacuum

Sources & evidence

ORD record
ord-91fcaac888604f7facd7ddf0279be558
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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