Trifluoroacetic acid → HCID 59613502, compound

HRID 384689Notes

Reaction equation

HRID 384689 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17]2[CH:22]=[C:21]([NH:23][CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[C:20]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)=[CH:19][N:18]=2)=[N:14][CH:15]=1)#[N:9]>ClCCl>[CH3:44][O:43][C:40]1[CH:41]=[CH:42][C:37]([C:20]2[C:21]([NH:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:22][C:17]([NH:16][C:13]3[N:14]=[CH:15][C:10]([C:8]#[N:9])=[N:11][CH:12]=3)=[N:18][CH:19]=2)=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613443HCID 59613443, compound

Product 1

HCID 59613502HCID 59613502, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.1 μL, 1.298 μmol) was added to tert-butyl 4-(2-(5-cyanopyrazin-2-ylamino)-5-(4-methoxyphenyl)pyridin-4-ylamino)piperidine-1-carboxylate (4 mg, 7.97 μmol) dissolved in dichloromethane (0.45 mL) and the mixture was stirred for 1 hr. The mixture was concentrated and purified by ion exchange on (solute SCX II acidic resin (1 g), eluting with MeOH then 2M NH3-MeOH. The basic fractions were combined and concentrated. Preparative thin layer chromatography, eluting with 10% MeOH/1% NH3/89% dichloromethane) gave 5-(5-(4-methoxyphenyl)-4-(piperidin-4-ylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile (2 mg, 4.98 μmol, 62.5% yield) as a yellow powder.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by ion exchange on (solute SCX II acidic resin (1 g)
  3. washeluting with MeOH
  4. concentrationconcentrated
  5. washPreparative thin layer chromatography, eluting with 10% MeOH/1% NH3/89% dichloromethane)

Sources & evidence

ORD record
ord-597b9bd18eb842978b9afdc74bb8c792
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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