Trifluoroacetic acid → HCID 66628192, compound

HRID 1046889Notes

Reaction equation

HRID 1046889 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][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[N:19]=[C:6]2[N:5]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[C:4]=1[CH3:39])#[N:2].FC(F)(F)C(O)=O>ClCCl>[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][CH2:21][C:22]([OH:24])=[O:23])[N:19]=[C:6]2[N:5]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:38])[F:36])[CH:30]=2)[C:4]=1[CH3:39])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 46841208HCID 46841208, compound

Product 1

HCID 66628192HCID 66628192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon protective gas, tert-butyl N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinate (18.0 mg, 34 μmol) was dissolved in dry dichloromethane (3.1 ml). At room temperature, trifluoroacetic acid (1.6 ml) was added, and the mixture was stirred for 45 min. More trifluoroacetic acid (2 ml) was then added, and the mixture was stirred for a further 30 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 (15.2 mg, 94% of theory).

Workup

  1. stirringthe mixture was stirred for a further 30 min
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (15.2 mg, 94% of theory)

Sources & evidence

ORD record
ord-c58c12e4f04748ad94ce2a800a2f5787
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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