(3R)-3-Methylpiperazin-2-one → HCID 50913308, compound
Reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C@H:11]([C:13]3[C:14]([F:24])=[C:15]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:25][C@H:26]1[NH:31][CH2:30][CH2:29][NH:28][C:27]1=[O:32]>>[F:24][C:14]1[C:13]([C@@H:11]([C:8]2[N:6]3[N:7]=[C:2]([N:31]4[CH2:30][CH2:29][NH:28][C:27](=[O:32])[C@H:26]4[CH3:25])[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH3:12])=[C:22]([F:23])[CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[N:19]2Participants
3
Procedure
The title compound was prepared in analogy to Example 18, using enantiomerically pure 6-[(S)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-5,7-difluoro-quinoline (Intermediate B, 50 mg, 0.145 mmol) and (R)-3-methyl-piperazin-2-one (33.1 mg, 0.29 mmol) instead of the racemates and flash chromatography for the purification. 2:1 mixture of title compound with compound of Example 60 (tR 3.59 min (conditions 5), tR 8.66 and 10.19 min (conditions 3, 90% n-hexane and 10% isopropanol), MH+=423.1, 1H-NMR in DMSO-d6: 8.91 (m, 1H); 8.42 (d, 1H); 7.90 (s, 1H); 7.80 (d, 1H); 7.69-7.50 (m, 3H); 7.05 (d, 1H); 4.93 (m, 1H); 4.50 and 4.28 (q, 1H); 3.87 (m, 1H); 3.43-2.89 (m, 3H); 1.84 (m, 3H); 1.30 and 0.93 (d, 3H)).
Workup
- customfor the purification
- addition2:1 mixture of title compound with compound of Example 60 (tR 3.59 min (conditions 5), tR 8.66 and 10.19 min (conditions 3, 90% n-hexane and 10% isopropanol), MH+=423.1, 1H-NMR in DMSO-d6: 8.91 (m, 1H); 8.42 (d, 1H); 7.90 (s, 1H); 7.80 (d, 1H); 7.69-7.50 (m, 3H); 7.05 (d, 1H); 4.93 (m, 1H); 4.50 and 4.28 (q, 1H); 3.87 (m, 1H); 3.43-2.89 (m, 3H); 1.84 (m, 3H); 1.30 and 0.93 (d, 3H))
Sources & evidence
- ORD record
- ord-4590866ed5a3424b92f7c55c63f2f35f
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389526B2
Reaction notes
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