1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid → 8-Oxo-5-(1-phenyl-cyclopentylmethyl)-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:28])[C:8]2[C:9]([N:14]([CH2:16][C:17]3([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:21][CH2:20][CH2:19][CH2:18]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>>[O:28]=[C:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][N:13]=2)[N:14]([CH2:16][C:17]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:18][CH2:19][CH2:20][CH2:21]2)[CH:15]=[C:6]1[C:4]([OH:5])=[O:3]Participants
3
Reactant 2
Product 1
Procedure
8-Oxo-5-(1-phenyl-cyclopentylmethyl)-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid (17) (70 mg, 14%) was synthesized as a yellow solid from 550 mg of 8-oxo-5-(1-phenyl-cyclopentylmethyl)-5,8-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid ethyl ester (16) 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-60917b1e82ea4483bd09175eff748f26
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199987B2
Reaction notes
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