Trifluoroacetic acid → HCID 59613357, compound

HRID 384708Notes

Reaction equation

HRID 384708 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](/[CH:38]=[CH:39]/[CH2:40][O:41][CH3:42])=[CH:19][N:18]=2)=[N:14][CH:15]=1)#[N:9]>ClCCl>[CH3:42][O:41][CH2:40]/[CH:39]=[CH: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 59613353HCID 59613353, compound

Product 1

HCID 59613357HCID 59613357, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.2 mL) was added at room temperature to a solution of (E)-tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-methoxyprop-1-enyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (0.020 g, 0.041 mmol) in dichloromethane (2 mL). The reaction mixture was stirred for 20 min. Solvent was removed in vacuo and the 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 the solvent was removed in vacuo. The crude product was purified by preparative thin layer chromatography, eluting with methanol/dichloromethane/NH3 (9%/90%/1%) to give the title compound as a yellow solid (0.008 g, 51%).

Workup

  1. customSolvent was removed in vacuo
  2. customthe mixture was purified by ion exchange on SCX-II acidic resin (500 mg)
  3. washeluting with methanol
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by preparative thin layer chromatography
  6. washeluting with methanol/dichloromethane/NH3 (9%/90%/1%)

Sources & evidence

ORD record
ord-e27477a6fb4440f69652c7ccbb026f0e
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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