Ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate → 7-Methyl-4-(5-methyl-2-phenylsulfanyl-phenylamino)-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)=[O:5])[CH3:2].[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:23]([NH2:25])[CH:24]=1>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:25][C:23]1[CH:24]=[C:19]([CH3:18])[CH:20]=[CH:21][C:22]=1[S:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)=[O:5])[CH3:2]Participants
3
Procedure
The product from Example 20a (438 mg, 2.03 mmol) was reacted with the product from Example 7f (510 mg, 2.03 mmol) for 10 min following the procedure from Example 7g giving the title compound which was purified by silica gel column chromatography eluting with 4% MeOH/CH2Cl2 as a solid (114 mg, 57%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.33 (t, J=6.99 Hz, 3 H) 2.16 (s, 3 H) 2.62 (s, 3 H) 4.29 (q, J=7.11 Hz, 2 H) 6.86 (s, 1 H) 7.04 (d, J=8.09 Hz, 1 H) 7.15-7.34 (m, 6 H) 7.39 (d, J=7.72 Hz, 1 H) 7.69 (d, J=8.82 Hz, 1 H) 9.17 (s, 1 H) 10.13 (s, 1 H); MS (ESI+) m/z 430 (M+H)+, (ESI−) m/z 428 (M−H)−.
Sources & evidence
- ORD record
- ord-6c41697a5b9e49c29d520afed5d85ed0
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236950B2
Reaction notes
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