Trifluoroacetic acid → HCID 59613513, compound

HRID 384673Notes

Reaction equation

HRID 384673 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[C:13]([C:31]3[O:35][N:34]=[C:33]([CH3:36])[N:32]=3)=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[CH3:36][C:33]1[N:32]=[C:31]([C:13]2[C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:15][C:10]([NH:9][C:6]3[N:7]=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=3)=[N:11][CH:12]=2)[O:35][N:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613367tert-Butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 59613513HCID 59613513, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (9 mg, 0.018 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (0.15 mL) at r.t. After 3 hr, the solution was evaporated to dryness and 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 to give the title compound as a yellow solid (4 mg, 56%).

Workup

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

Sources & evidence

ORD record
ord-4de76c1b15804ce5bcdc1e3726bffb23
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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