Trifluoroacetic acid → HCID 58431290, compound

HRID 1617356Notes

Reaction equation

HRID 1617356 reaction equation
[C:1]([CH2:3][C:4]1([N:27]2[CH:31]=[C:30]([C:32]3[C:33]4[CH:40]=[CH:39][N:38](COCC[Si](C)(C)C)[C:34]=4[N:35]=[CH:36][N:37]=3)[CH:29]=[N:28]2)[CH2:7][N:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[C:23]([F:26])([F:25])[F:24])=[O:15])[CH2:10][CH2:9]2)[CH2:5]1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([CH2:3][C:4]1([N:27]2[CH:31]=[C:30]([C:32]3[C:33]4[CH:40]=[CH:39][NH:38][C:34]=4[N:35]=[CH:36][N:37]=3)[CH:29]=[N:28]2)[CH2:7][N:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[C:23]([F:25])([F:26])[F:24])=[O:15])[CH2:10][CH2:9]2)[CH2:5]1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58431402HCID 58431402, compound

Product 1

HCID 58431290HCID 58431290, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 20 mL vial was charged with 4-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[3-(trifluoromethyl)pyridin-4-yl]piperidine-1-carboxamide (56 mg, 0.1 mmol), trifluoroacetic acid (1.5 mL, 19 mmol) and methylene chloride (1.5 mL). The mixture was stirred at room temperature for 1 hour and concentrated in vacuum. The residue was dissolved in 3 mL of a methanol solution containing 20% ethylenediamine. After being stirred at room temperature for 1 hour, HPLC purification (method B) gave the title compound 4-{3-(cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[3-(trifluoromethyl)pyridin-4-yl]piperidine-1-carboxamide. LC-MS: 551.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuum
  2. dissolutionThe residue was dissolved in 3 mL of a methanol solution
  3. additioncontaining 20% ethylenediamine
  4. stirringAfter being stirred at room temperature for 1 hour
  5. customHPLC purification (method B)

Sources & evidence

ORD record
ord-cc5932c2043c4cfbac0afd4e7ff0fee9
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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