Methyl 4-aminobenzoate → Methyl ({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[tetrahydro-2H-pyran-2-yl]propanoyl}amino)benzoate

HRID 56788

Reaction equation

HRID 56788 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]#[N:29])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[C:17](O)=[O:18])[C:10](=[O:27])[CH:9]=2)[CH:7]=1.N[C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1.CC(C)[N:43]=C=NC(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]#[N:29])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[C:17]([NH:43][C:39]3[CH:40]=[CH:31][CH:32]=[CH:33][C:34]=3[C:35]([O:37][CH3:38])=[O:36])=[O:18])[C:10](=[O:27])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 12734DiisopropylcarbodiimideHCID 1176226812-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[tetrahydro-2H-pyran-2-yl]propanoic acid

Product 1

HCID 131736942Methyl ({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[tetrahydro-2H-pyran-2-yl]propanoyl}amino)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.20 g (5.28 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[tetrahydro-2H-pyran-2-yl]propanoic acid (mixture of racemic diastereomers), 798 mg (5.28 mmol) of methyl 4-aminobenzoate, 750 mg (5.28 mmol) of Oxima and 822 μl (5.28 mmol) of DIC in 110 ml of dimethylformamide were reacted according to General Method 5B. The reaction mixture was purified by flash chromatography (80 g cartridge, 60 ml/min, cyclohexane/ethyl acetate gradient). Yield: 905 mg (31% of theory)

Workup

  1. customThe reaction mixture was purified by flash chromatography (80 g cartridge, 60 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-dbbe3062c8614077a69660130c1968ac
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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