1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid → 5-Biphenyl-2-ylmethyl-8-oxo-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid

HRID 1497678Notes

Reaction equation

HRID 1497678 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:29])[C:8]2[C:9]([N:14]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:15]=1)=[N:10][CH:11]=[CH:12][N:13]=2)=[O:5])C.C1(C2C=CC=CC=2)C=CC=CC=1CN1C2C(=NC=CC=2)C(=O)C(C(O)=O)=C1>>[C:18]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][N:14]1[C:9]2=[N:10][CH:11]=[CH:12][N:13]=[C:8]2[C:7](=[O:29])[C:6]([C:4]([OH:5])=[O:3])=[CH:15]1

Participants

3

Reactant 2

HCID 769024811-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acidHCID 769028645-Biphenyl-2-ylmethyl-8-oxo-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid ethyl ester

Product 1

HCID 769024835-Biphenyl-2-ylmethyl-8-oxo-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acidYield 54%

Procedure

5-Biphenyl-2-ylmethyl-8-oxo-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid (15) (300 mg, 54%) was synthesized as a light yellow solid from 600 mg of 5-biphenyl-2-ylmethyl-8-oxo-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid ethyl ester (14) following the procedure described for 1-biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid (7).

Sources & evidence

ORD record
ord-4b93e674022e466b8cd3302485608ebe
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Reaction notes

Loading…