Trifluoroacetic acid → HCID 86660770, compound

HRID 1046864Notes

Reaction equation

HRID 1046864 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([NH:11][C:12]1[N:41]=[C:15]2[N:16]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[C:17]([CH3:30])=[C:18]([C:28]#[N:29])[C@@H:19]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[N:14]2[N:13]=1)=[O:10])(C)(C)C.[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:28]([C:18]1[C@@H:19]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)[N:14]2[N:13]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][NH2:7])[N:41]=[C:15]2[N:16]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:39])([F:40])[F:38])[CH:32]=2)[C:17]=1[CH3:30])#[N:29]

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-ff85aa02f5b64402b9a36542d0f18af9
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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