Trifluoroacetic acid → HCID 86298155, compound

HRID 57041Notes

Reaction equation

HRID 57041 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:42]#[N:43])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:33][C:34]3([C:37]([F:40])([F:39])[F:38])[CH2:36][CH2:35]3)[C:17]([NH:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26]C(C)(C)C)=[O:25])=[CH:22][CH:21]=3)=[O:18])[C:10](=[O:41])[CH:9]=2)[CH:7]=1.FC(F)(F)C(O)=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:42]#[N:43])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:33][C:34]3([C:37]([F:39])([F:40])[F:38])[CH2:36][CH2:35]3)[C:17]([NH:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)=[O:18])[C:10](=[O:41])[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622767HCID 117622767, compound

Product 1

HCID 86298155HCID 86298155, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent4×

Procedure

157 mg (255 μmol) of tert-butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[1-(trifluoromethyl)cyclopropyl]propanoyl}amino)benzoate (racemate) were hydrolysed with 393 μl (5.10 mmol) of trifluoroacetic acid according to General Method 2, and after preparative HPLC [column: Chromatorex C18, 10 μm, 125 mm×30 mm, mobile phase: acetonitrile/0.1% formic acid gradient (0 to 3 min 10% acetonitrile, to 35 min 90% acetonitrile and a further 3 min 90% acetonitrile)], the title compound was obtained. Yield: 94 mg (65% of theory)

Sources & evidence

ORD record
ord-939b34420d4348679619b4ca6833fb8b
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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