Trifluoroacetic acid → HCID 117622788, compound

HRID 57023Notes

Reaction equation

HRID 57023 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]#[N:40])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:33][C:34]3([CH3:37])[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:38])[CH:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]#[N:40])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:33][C:34]3([CH3:37])[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:38])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622757HCID 117622757, compound

Product 1

HCID 117622788HCID 117622788, compound

Procedure

100 mg (178 μmol) of tert-butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1-methylcyclopropyl)propanoyl}amino)benzoate (racemate) and 274 μl (3.56 mmol) of TFA were reacted according to General Method 2. The reaction mixture was purified by preparative HPLC [column: Chromatorex C18, 10 μm, 125 mm×30 mm, mobile phase: acetonitrile/water gradient (0 to 3 min 15% acetonitrile, to 35 min 90% acetonitrile and a further 3 min 90% acetonitrile)]. Yield: 107 mg (27% of theory)

Workup

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

Sources & evidence

ORD record
ord-385ad49db00c426ba3c190bf52e42414
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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