Trifluoroacetic acid → 5-(5-Chloro-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile

HRID 556855Notes

Reaction equation

HRID 556855 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]2)=[CH:11][C:12]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22]#[N:23])=[CH:18][N:17]=2)=[N:13][CH:14]=1>ClCCl>[Cl:8][C:9]1[C:10]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:11][C:12]([NH:15][C:16]2[N:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613464Tert-butyl 4-((5-chloro-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 596134675-(5-Chloro-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrileYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.1 mL) was added to tert-butyl 4-((5-chloro-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (12 mg, 0.027 mmol) in dichloromethane (1 mL) and the mixture was stirred at r.t. for 2 hr. Solvent was removed in vacuo and the residue was redissolved in MeOH and adsorbed onto Isolute SCX-II acidic resin (500 mg). The resin was washed with methanol, then 2M ammonia in methanol. The basic fractions were evaporated to dryness to give 5-(5-chloro-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile (2 mg, 22%) as a yellow powder.

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue was redissolved in MeOH
  3. washThe resin was washed with methanol
  4. customThe basic fractions were evaporated to dryness

Sources & evidence

ORD record
ord-30a3613f80744ec4a823e3c24c2b0e86
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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