Trifluoroacetic acid → HCID 117622589, compound

HRID 56816Notes

Reaction equation

HRID 56816 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:30]#[N:31])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:24][C:25]3([CH3:28])[CH2:27][CH2:26]3)[C:17]([O:19]C(C)(C)C)=[O:18])[C:10](=[O:29])[CH:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:30]#[N:31])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:24][C:25]3([CH3:28])[CH2:27][CH2:26]3)[C:17]([OH:19])=[O:18])[C:10](=[O:29])[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622586tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1-methylcyclopropyl)propanoate

Product 1

HCID 117622589HCID 117622589, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

247 mg (558 μmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1-methylcyclopropyl)propanoate (racemate) in 1 ml of dichloromethane and 859 μl (11.2 mmol) of TFA were reacted according to General Method 6A. The crude product was purified by preparative HPLC [column: Chromatorex C18, 10 μm, 125×30 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)]. Yield: 95 mg (43% of theory)

Workup

  1. customThe crude product was purified by preparative HPLC [column
  2. customa further 3 min 90% acetonitrile

Sources & evidence

ORD record
ord-80fea362831147df8e4cf30d35740758
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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