1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester → 8-Oxo-5-(1-phenyl-cyclopentylmethyl)-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid ethyl ester

HRID 1497679Notes

Reaction equation

HRID 1497679 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([C:10]([C:12]1[C:17](Cl)=[N:16][CH:15]=[CH:14][N:13]=1)=[O:11])=[CH:6][N:7]([CH3:9])C)[CH3:2].C(OC(C1C(=O)C2C(=CC=CN=2)N(CC2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)C=1)=O)C>>[CH2:1]([O:3][C:4]([C:5]1[C:10](=[O:11])[C:12]2[C:17]([N:7]([CH2:9][C:38]3([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[CH2:39][CH2:40][CH2:41][CH2:42]3)[CH:6]=1)=[N:16][CH:15]=[CH:14][N:13]=2)=[O:19])[CH3:2]

Participants

3

Reactant 2

HCID 867254331-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl esterHCID 867254372-(3-Chloro-pyrazine-2-carbonyl)-3-dimethylamino-acrylic acid ethyl ester

Product 1

HCID 867254388-Oxo-5-(1-phenyl-cyclopentylmethyl)-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid ethyl esterYield 30%

Procedure

8-Oxo-5-(1-phenyl-cyclopentylmethyl)-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid ethyl ester (16) (600 mg, 30%) was synthesized as a brown sticky liquid from 1.5 g of 2-(3-chloro-pyrazine-2-carbonyl)-3-dimethylamino-acrylic acid ethyl ester (13) following the procedure described for 1-biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester (6).

Sources & evidence

ORD record
ord-3eead7ad4d564a8a9b9d78d951617389
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Reaction notes

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