Trifluoroacetic acid → 2-Furan-2-yl-6-piperazin-1-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

HRID 2242908Notes

Reaction equation

HRID 2242908 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[C:16]([NH:28]C(OC(C)(C)C)=O)[C:17]3[N:18]([N:20]=[C:21]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[C:21]1[N:22]=[C:17]2[C:16]([NH2:28])=[N:15][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:19][N:18]2[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 685441504-(8-Tert-butoxycarbonylamino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 111619332-Furan-2-yl-6-piperazin-1-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(8-tert-butoxycarbonylamino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester (140 mg, 0.29 mmol; see Example 16 (i) above) in methylene chloride (4 mL) was added trifluoroacetic acid (400 μL). The reaction was stirred at room temperature for 2 hours. After the solvent and extra trifluoroacetic acid was evaporated, the residue was dissolved in methylene chloride (4 mL). The title compound in methylene chloride was divided into two portions and used for further reactions (see Example 17 and Example 18 below) without further purification.

Workup

  1. customAfter the solvent and extra trifluoroacetic acid was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride (4 mL)
  3. customused for further reactions (see Example 17 and Example 18 below) without further purification

Sources & evidence

ORD record
ord-c8aa57986f73411abc9241d510029279
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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