Trifluoroacetic acid → Methyl 4-(3-amino-6-(1,4,5,6-tetrahydropyridin-3-yl)pyrazin-2-yl)-2-fluorobenzoate

HRID 596089Notes

Reaction equation

HRID 596089 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:19]2[CH2:20][CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH:24]=2)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[C:10]([F:18])[CH:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[C:10]([F:18])[CH:9]=2)=[N:6][C:5]([C:19]2[CH2:20][CH2:21][CH2:22][NH:23][CH:24]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118045639tert-butyl 5-(5-amino-6-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 118046128Methyl 4-(3-amino-6-(1,4,5,6-tetrahydropyridin-3-yl)pyrazin-2-yl)-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-(5-amino-6-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate (150 mg, 0.350 mmol) (inseparable mixture) in DCM (4 mL) was added TFA (1 mL, 12.98 mmol). The reaction mixture was stirred at room temperature for 30-45 min. The reaction mixture was evaporated on rotovap, and azeotroped with toluene. The crude product was proceeded to next step without purification. LCMS (m/z): 329.2 (MH+), 0.502 min.

Workup

  1. customThe reaction mixture was evaporated on rotovap
  2. customazeotroped with toluene
  3. customThe crude product was proceeded to next step without purification
  4. custom329.2 (MH+), 0.502 min.

Sources & evidence

ORD record
ord-52c4d75ceb9a4b81869fac00ab548bf2
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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