Trifluoroacetic acid → HCID 86660770, compound

HRID 2200964Notes

Reaction equation

HRID 2200964 reaction equation
[C:1]([C:3]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:7]2[N:17]=[C:18]([NH:20][C:21](=[O:31])[CH2:22][NH:23]C(=O)OC(C)(C)C)[N:19]=[C:6]2[N:5]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)[C:4]=1[CH3:42])#[N:2].[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46]>ClCCl>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[C:1]([C:3]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:7]2[N:17]=[C:18]([NH:20][C:21](=[O:31])[CH2:22][NH2:23])[N:19]=[C:6]2[N:5]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=2)[C:4]=1[CH3:42])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86660771HCID 86660771, compound

Product 1

HCID 86660770HCID 86660770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon protective gas, tert-butyl [2-((7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamino)-2-oxoethyl]carbamate (6.4 mg, 11 μmol) was dissolved in dry dichloromethane (5 ml). At room temperature, trifluoroacetic acid (1 ml) was added, and the mixture was stirred for 40 min. The reaction mixture was then concentrated under reduced pressure and the residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (˜6 mg, quant.).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  3. customAfter lyophilization, the product was obtained as a solid (˜6 mg, quant.)

Sources & evidence

ORD record
ord-0d9874249b38449ea63ed751c6a50255
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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