Trifluoroacetic acid → 5-(5-(3-Hydroxy-3-methylbut-1-ynyl)-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile

HRID 384711

Reaction equation

HRID 384711 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17]2[CH:22]=[C:21]([NH:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)[C:20]([C:38]#[C:39][C:40]([OH:43])([CH3:42])[CH3:41])=[CH:19][N:18]=2)=[N:14][CH:15]=1)#[N:9]>ClCCl>[OH:43][C:40]([CH3:42])([CH3:41])[C:39]#[C:38][C:20]1[C:21]([NH:23][CH2:24][CH:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]2)=[CH:22][C:17]([NH:16][C:13]2[N:14]=[CH:15][C:10]([C:8]#[N:9])=[N:11][CH:12]=2)=[N:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613530tert-Butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-hydroxy-3-methylbut-1-ynyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 596133865-(5-(3-Hydroxy-3-methylbut-1-ynyl)-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.2 mL) was added at room temperature to a solution of tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-hydroxy-3-methylbut-1-ynyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (0.020 g, 0.041 mmol) dissolved in dichloromethane (2 mL). The reaction mixture was stirred for 20 min. Solvent was removed in vacuo and the crude mixture was purified by ion exchange on SCX-II acidic resin (500 mg), eluting with methanol then 2M ammonia-methanol. The basic fractions were combined and solvent was removed in vacuo. The crude product was purified by preparative thin layer chromatography, eluting with methanol/dichloromethane (1/19), to give the title compound as a yellow solid (0.008 g, 50%).

Workup

  1. customSolvent was removed in vacuo
  2. customthe crude mixture was purified by ion exchange on SCX-II acidic resin (500 mg)
  3. washeluting with methanol
  4. customsolvent was removed in vacuo
  5. customThe crude product was purified by preparative thin layer chromatography
  6. washeluting with methanol/dichloromethane (1/19)

Sources & evidence

ORD record
ord-3fd9a182b05f4c0ebd28ac1143b6ec18
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Linked notes

Loading…