Trifluoroacetic acid → Methyl 6-[(5-cyano-2-pyrazinyl)amino]-4-[(4-piperidinylmethyl)amino]nicotinate

HRID 384636Notes

Reaction equation

HRID 384636 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][C:23]2[C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][N:26]=[C:25]([NH:33][C:34]3[CH:39]=[N:38][C:37]([C:40]#[N:41])=[CH:36][N:35]=3)[CH:24]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[C:40]([C:37]1[N:38]=[CH:39][C:34]([NH:33][C:25]2[CH:24]=[C:23]([NH:22][CH2:21][CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)[C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][N:26]=2)=[N:35][CH:36]=1)#[N:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613326Methyl 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinate

Product 1

HCID 42610232Methyl 6-[(5-cyano-2-pyrazinyl)amino]-4-[(4-piperidinylmethyl)amino]nicotinateYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.1 mL) was added to a solution of methyl 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinate (20 mg, 0.04 mmol) in dichloromethane (1 mL) at room temperature. After 20 minutes, the solution was evaporated to dryness and purified by ion exchange chromatography 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 methyl 6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-4-ylmethylamino)-nicotinate compound as a yellow solid (11 mg, 70%).

Workup

  1. customthe solution was evaporated to dryness
  2. custompurified by ion exchange chromatography on SCX-II acidic resin (500 mg)
  3. washeluting with methanol
  4. customsolvent was evaporated

Sources & evidence

ORD record
ord-aa3e919bb8014839b9d0b0d039a7c8f7
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

Loading…