Trifluoroacetic acid → HCID 42610297, compound

HRID 384638Notes

Reaction equation

HRID 384638 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](=[O:46])[NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:19][N:18]=2)=[N:14][CH:15]=1)#[N:9]>ClCCl>[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][NH:28][CH2:27][CH2:26]3)[C:20]([C:38]([NH:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[O:46])=[CH:19][N:18]=2)=[N:14][CH:15]=1)#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613455Tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(phenylcarbamoyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 42610297HCID 42610297, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.05 mL) was added to a solution of tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(phenylcarbamoyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (11.0 mg, 0.02 mmol) in dichloromethane (0.5 mL) at room temperature. After 20 minutes, solvent was evaporated and the crude product 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 evaporated to give 6-(5-cyanopyrazin-2-ylamino)-N-phenyl-4-(piperidin-4-ylmethylamino)nicotinamide as a yellow solid (5.6 mg, 63%).

Workup

  1. customsolvent was evaporated
  2. customthe crude product was purified by ion exchange on SCX-II acidic resin (500 mg)
  3. washeluting with methanol
  4. customsolvent was evaporated

Sources & evidence

ORD record
ord-f7618e3c0c06454d841b6b9bd9664ab5
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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