Trifluoroacetic acid → HCID 72704325, compound

HRID 1054934Notes

Reaction equation

HRID 1054934 reaction equation
COC1C=CC(C[N:8]2[C:12]([CH2:13][CH2:14][C:15]3[N:25]=[C:18]4[C:19]([CH3:24])=[N:20][CH:21]=[C:22]([CH3:23])[N:17]4[N:16]=3)=[N:11][C:10]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:9]2)=CC=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>ClCCl>[CH3:23][C:22]1[N:17]2[N:16]=[C:15]([CH2:14][CH2:13][C:12]3[NH:8][N:9]=[C:10]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[N:11]=3)[N:25]=[C:18]2[C:19]([CH3:24])=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 72704533HCID 72704533, compound

Product 1

HCID 72704325HCID 72704325, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-(1-(4-methoxybenzyl)-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (13.6 mg, 31.4 μmol, Eq: 1.00) was stirred with trifluoroacetic acid (143 mg, 96.3 μl, 1.26 mmol, Eq: 40) and anisole (61.2 mg, 61.8 μl, 566 μmol, Eq: 18) in Dichloromethane (400 μl) overnight at room-temperature. The reaction mixture was extracted with aq. sodium borohydride sat. and dichloromethane three times, dried over magnesium sulfate, filtered and evaporated to give 5,8-Dimethyl-2-[2-(5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-ethyl]-[1,2,4]triazolo[1,5-a]pyrazine (6.6 mg, 67.2%) as off-white solid.

Workup

  1. extractionThe reaction mixture was extracted with aq. sodium borohydride sat. and dichloromethane three times
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-0e9c77ad54b548118d816db80270a231
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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