[(E)-1-aminoethylideneamino] 6-[(5-cyanopyrazin-2-yl)amino]-4-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methylamino]pyridine-3-carboxylate → tert-Butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 384672Notes

Reaction equation

HRID 384672 reaction equation
[NH2:1]/[C:2](=[N:4]/[O:5][C:6]([C:8]1[C:9]([NH:23][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[CH:10][C:11]([NH:14][C:15]2[CH:20]=[N:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=2)=[N:12][CH:13]=1)=O)/[CH3:3]>N1C=CC=CC=1>[C:21]([C:18]1[N:19]=[CH:20][C:15]([NH:14][C:11]2[CH:10]=[C:9]([NH:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:27][CH2:26]3)[C:8]([C:6]3[O:5][N:4]=[C:2]([CH3:3])[N:1]=3)=[CH:13][N:12]=2)=[N:16][CH:17]=1)#[N:22]

Participants

3

Reactant 1

HCID 59613429[(E)-1-aminoethylideneamino] 6-[(5-cyanopyrazin-2-yl)amino]-4-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methylamino]pyridine-3-carboxylate

Product 1

HCID 59613367tert-Butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylateYield 23.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (E)-tert-Butyl 4-((5-((1-aminoethylideneaminooxy)carbonyl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (40 mg, 0.078 mmol) in pyridine (3 mL) was heated at 120° C. for 8 hr using microwave irradiation. After evaporation of the solvent, the crude product was purified by column chromatography (Biotage), eluting with EtOAc/n-hexane (1/1), to give the title compound as a yellow solid (9 mg, 23%).

Workup

  1. custommicrowave irradiation
  2. customAfter evaporation of the solvent
  3. customthe crude product was purified by column chromatography (Biotage)
  4. washeluting with EtOAc/n-hexane (1/1)

Sources & evidence

ORD record
ord-a862d2f9379145ca8f648abb7965774a
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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