HCID 59613353, compound → HCID 59613471, compound

HRID 384709Notes

Reaction equation

HRID 384709 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](/[CH:31]=[CH:32]/[CH2:33][O:34][CH3:35])=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2]>[Pd].CO>[CH3:35][O:34][CH2:33][CH2:32][CH2:31][C:13]1[C:14]([NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)=[CH:15][C:10]([NH:9][C:6]2[N:7]=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=2)=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 59613353HCID 59613353, compound

Product 1

HCID 59613471HCID 59613471, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (E)-tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-methoxyprop-1-enyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (Synthesis 183-B) (0.035 g, 0.073 mmol), palladium on carbon (0.035 g) in methanol (2 mL) was stirred overnight under hydrogen (1 atm). The reaction mixture was filtered through celite and the solvent was removed in vacuo. The crude product was used without further purification. TFA (0.2 mL) was added to a solution of the crude material dissolved in dichloromethane (2 mL) at room temperature. 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/dichloromethan/NH3 (9%/90%/1%), to give the title compound as a yellow solid (0.020 g, 84%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was removed in vacuo
  3. customThe crude product was used without further purification
  4. additionTFA (0.2 mL) was added to a solution of the crude material
  5. dissolutiondissolved in dichloromethane (2 mL) at room temperature
  6. customSolvent was removed in vacuo
  7. customthe mixture was purified by ion exchange on SCX-II acidic resin (500 mg)
  8. washeluting with methanol
  9. customthe solvent was removed in vacuo
  10. customThe crude product was purified by preparative thin layer chromatography
  11. washeluting with methanol/dichloromethan/NH3 (9%/90%/1%)

Sources & evidence

ORD record
ord-42c146c3f96c47208fa8a5b7818e4f26
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

Loading…