Acetic Acid → 6-[4-(5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethyl)-piperazin-1-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

HRID 2242910Notes

Reaction equation

HRID 2242910 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:21]=[C:9]2[C:10]([NH2:20])=[N:11][C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:13][N:8]2[N:7]=1.[Cl:22][C:23]1[N:27]([CH3:28])[N:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:24]=1[CH:33]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[Cl:22][C:23]1[N:27]([CH3:28])[N:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:24]=1[CH2:33][N:17]1[CH2:18][CH2:19][N:14]([C:12]2[N:11]=[C:10]([NH2:20])[C:9]3[N:8]([N:7]=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[N:21]=3)[CH:13]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14784595-Chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 111619332-Furan-2-yl-6-piperazin-1-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

Product 1

HCID 114090446-[4-(5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethyl)-piperazin-1-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamineYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-furan-2-yl-6-piperazin-1-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine in methylene chloride (see Example 16 above) was added 5-chloro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxaldehyde (45 mg, 0.21 mmol), sodium triacetoxyborohydride (65 mg, 0.31 mmol) and acetic acid (12 μL, 0.2 mmol). The reaction was stirred at room temperature overnight. After the solvent was removed, the residue was subjected to flash chromatography (ethyl acetate/hexanes=40:60) to afford 6-[4-(5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethyl)-piperazin-1-yl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine as a white solid (9 mg, 13%).

Workup

  1. customAfter the solvent was removed

Sources & evidence

ORD record
ord-bdd2f04487b64808aa177efef6743a7a
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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