Trifluoroacetic acid → 5-((5-Amino-4-(piperidin-4-ylmethoxy)pyridin-2-yl)amino)pyrazine-2-carbonitrile

HRID 556812Notes

Reaction equation

HRID 556812 reaction equation
[NH2:1][C:2]1[C:3]([O:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[N:13][C:12]([C:15]#[N:16])=[CH:11][N:10]=2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[C:3]([O:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:4][C:5]([NH:8][C:9]2[N:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613369tert-Butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-yloxy)methyl)piperidine-1-carboxylate

Product 1

HCID 426103575-((5-Amino-4-(piperidin-4-ylmethoxy)pyridin-2-yl)amino)pyrazine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-yloxy)methyl)piperidine-1-carboxylate (16 mg, 0.038 mmol) in 10 mL dichloromethane (10 mL) was treated over 45 minutes with 2 mL trifluoroacetic acid. After concentration of the solution in vacuo, the required product was isolated by SPE using a MP-TsOH cartridge, eluting with 2N ammonia in methanol. Concentration of the eluent gave the required product as a yellow solid (10 mg).

Sources & evidence

ORD record
ord-20a6bb48f0fa4f1d8f06609158b389c1
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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