Trifluoroacetic acid → 3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

HRID 1959367Notes

Reaction equation

HRID 1959367 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:10]=[CH:11][C:12]([C:26]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH:27]=2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][N:19]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:20]1([C:17]2[O:16][C:15]([C:14]3[C:9]([NH2:8])=[N:10][CH:11]=[C:12]([C:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH:27]=4)[N:13]=3)=[N:19][N:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66744435tert-butyl 4-(5-(bis(tert-butoxycarbonyl)amino)-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 461995573-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amineYield 152.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(5-(bis(tert-butoxycarbonyl)amino)-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.4 g, 3.867 mmol) was dissolved in DCM (40 mL) and treated with TFA (8 mL, 103.8 mmol). The reaction was allowed to stir overnight and then the solvent was removed in vacuo. The mixture was azeotroped with DCM (×3) and dried under vacuum to give the desired product as an orange solid (1.89 g, 100% Yield).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe mixture was azeotroped with DCM (×3)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-8158450220be45eeb414ea12c9d9d929
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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