Trifluoroacetic acid → 3-amino-6-(piperazin-1-yl)-N-(pyridin-2-yl)pyrazine-2-carboxamide

HRID 1959359Notes

Reaction equation

HRID 1959359 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][C:17]([NH2:20])=[C:16]([C:21](=[O:29])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO.C(Cl)Cl>[NH2:20][C:17]1[C:16]([C:21]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:29])=[N:15][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:19][N:18]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 66745477Tert-butyl 4-(5-amino-6-(pyridin-2-ylcarbamoyl)pyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 461995583-amino-6-(piperazin-1-yl)-N-(pyridin-2-yl)pyrazine-2-carboxamideYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Tert-butyl-4-[5-amino-6-(2-pyridylcarbamoyl)pyrazin-2-yl]piperazine-1-carboxylate (5.43 g, 13.59 mmol) was suspended in DCM (50 mL) and stirred at 0° C. during addition of TFA (10 ml). The reaction mixture was warmed to RT over 2 hours but analysis showed little deprotection. The reaction was treated with a further 30 ml of TFA and stirred at RT for 15 minutes. The mixture was concentrated under reduced pressure to give a dark red oil which was dissolved in MeOH/DCM and azeotroped with toluene to give an intense orange solid which was filtered, washed with ether and dried under high vacuum (5.41 g, 73% Yield).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a dark red oil which
  3. customazeotroped with toluene
  4. customto give an intense orange solid which
  5. filtrationwas filtered
  6. washwashed with ether
  7. customdried under high vacuum (5.41 g, 73% Yield)

Sources & evidence

ORD record
ord-1ca1c21b7275466299754c888b4db901
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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