Benzocaine → Ethyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4,4-trifluorobutanoyl}amino)benzoate

HRID 56799Notes

Reaction equation

HRID 56799 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]#[N:27])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:17]([OH:19])=O)[C:10](=[O:25])[CH:9]=2)[CH:7]=1.[NH2:28][C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]#[N:27])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:17]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:38][CH:39]=3)=[O:19])[C:10](=[O:25])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12734DiisopropylcarbodiimideHCID 117622865HCID 117622865, compound

Product 1

HCID 117622962Ethyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4,4-trifluorobutanoyl}amino)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

63.0 mg (157 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4,4-trifluorobutanoic acid (racemate), 26.0 mg (157 μmol) of ethyl 4-aminobenzoate, 22.3 mg (157 μmol) of Oxima and 24.0 μl (157 μmol) of DIC in 1.6 ml of dimethylformamide were reacted according to General Method 5B. The reaction product was purified by preparative HPLC [column: Chromatorex C18, 10 μm, 125×30 mm, mobile phase: acetonitrile/0.05% formic acid gradient (0 to 3 min 10% acetonitrile, to 35 min 90% acetonitrile and a further 3 min 90% acetonitrile)]. Yield: 25.1 mg (28% of theory)

Workup

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

Sources & evidence

ORD record
ord-9812e37926574f169fb20e859947b936
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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