Trifluoroacetic acid → HCID 73053317, compound

HRID 1497823Notes

Reaction equation

HRID 1497823 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[N:19]=[C:18]([C:20]2[C:21]([CH3:40])=[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[C:23]3[N:24]([N:26]=[C:27]([NH2:29])[N:28]=3)[CH:25]=2)[N:17]([C:41]2[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][CH:42]=2)[N:16]=1)(C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:14][C:15]1[N:19]=[C:18]([C:20]2[C:21]([CH3:40])=[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[C:23]3[N:24]([N:26]=[C:27]([NH2:29])[N:28]=3)[CH:25]=2)[N:17]([C:41]2[CH:42]=[CH:43][C:44]([C:47]#[N:48])=[CH:45][CH:46]=2)[N:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86708123HCID 86708123, compound

Product 1

HCID 73053317HCID 73053317, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of [5-[2-amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-1-(4-cyano-phenyl)-1H-[1,2,4]triazol-3-yl]-carbamic acid tert-butyl ester (Int. 38, 325 mg, 0.565 mmol) in DCM (5 mL) and the reaction mixture was stirred for 2.5 hrs. Saturated aqueous NaHCO3 solution (10 mL) was added and the phases were separated then the organics were concentrated in vacuo. The resulting residue was purified by HPLC, C 18 column, eluting with a gradient 40-80% MeCN in water (+0.1% formic acid) to give the title compound as a white solid (6 mg).

Workup

  1. customthe phases were separated
  2. concentrationthe organics were concentrated in vacuo
  3. customThe resulting residue was purified by HPLC, C 18 column
  4. washeluting with a gradient 40-80% MeCN in water (+0.1% formic acid)

Sources & evidence

ORD record
ord-417cfb2285dd41a5878a1febf0c1505d
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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