Benzocaine → HCID 117622446, compound

HRID 56867Notes

Reaction equation

HRID 56867 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:27]#[N:28])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]([O:24][CH3:25])[CH2:22][CH3:23])[C:17]([OH:19])=O)[C:10](=[O:26])[CH:9]=2)[CH:7]=1.[NH2:29][C:30]1[CH:40]=[CH:39][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:32][CH:31]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:27]#[N:28])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]([O:24][CH3:25])[CH2:22][CH3:23])[C:17]([NH:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:39][CH:40]=3)=[O:19])[C:10](=[O:26])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12734DiisopropylcarbodiimideHCID 117622447HCID 117622447, compound

Product 1

HCID 117622446HCID 117622446, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

620 mg (1.53 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxyhexanoic acid (mixture of racemic diastereomers), 253 mg (1.53 mmol) of ethyl 4-aminobenzoate, 218 mg (1.53 mmol) of Oxima and 239 μl (1.53 mmol) of DIC in 15.3 ml of dimethylformamide were reacted according to General Method 5B. The crude product was purified by flash chromatography (120 g cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient). Yield: 634 mg (70% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (120 g cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-d4552fd7460c46e6980c31e06242f0b5
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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