4-(3,4-dichlorophenyl)-2-((dimethylamino)methylene)-3,4-dihydronaphthalen-1(2H)-one → Tert-butyl 4-(6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)piperidine-1-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[C:11](=[CH:20]N(C)C)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[NH:25]([CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1)[C:26]([NH2:28])=[NH:27]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3[N:28]=[C:26]([NH:25][CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)[N:27]=[CH:20][C:11]=3[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Procedure
This was prepared from 4-(3,4-dichlorophenyl)-2-((dimethylamino)methylene)-3,4-dihydronaphthalen-1(2H)-one and tert-butyl 4-guanidinopiperidine-1-carboxylate hydrochloride salt under the condition described in the general procedure 1 to afford tert-butyl 4-(6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)piperidine-1-carboxylate (0.68 g) as a light yellow solid. M.p.=94-96° C. 1H NMR 400 MHz (DMSO-d6) δ 8.27-8.25 (m, 1 H), 8.13 (s, 1 H), 7.52 (d, J=8.4 Hz, 1 H), 7.47-7.40 (m, 3 H), 7.08-7.00 (m, 3 H), 4.40 (t, J=6.4 Hz, 1 H), 3.94 (bd, 2 H), 3.22-3.03 (m, 2 H), 2.90-2.85 (m, 2 H), 1.89-1.86 (m, 2 H), 1.42-1.34 (m, 12 H). LCMS m/e 525 (M+H).
Sources & evidence
- ORD record
- ord-545ebd5794434b85ad921d982c129b7f
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357694B2
Reaction notes
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