1-Methylpiperazine → 6-(3,4-dichlorophenyl)-N-(4-(2-(4-methylpiperazin-1-yl)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine
Reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:24]=[CH:23][C:22]3[CH2:21][CH:20]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=4)[C:19]4[CH:33]=[CH:34][CH:35]=[CH:36][C:18]=4[C:17]=3[N:16]=2)=[CH:10][CH:9]=1)(=O)=O.[CH3:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>>[Cl:32][C:27]1[CH:26]=[C:25]([CH:20]2[C:19]3[CH:33]=[CH:34][CH:35]=[CH:36][C:18]=3[C:17]3[N:16]=[C:15]([NH:14][C:11]4[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][N:41]5[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]5)=[CH:9][CH:10]=4)[N:24]=[CH:23][C:22]=3[CH2:21]2)[CH:30]=[CH:29][C:28]=1[Cl:31]Participants
Procedure
This product was synthesized as described in general procedure 2 except 4-(6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate was used instead of 4-(6-(3-bromophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate and N-methyl piperazine was used instead of piperidine to afford 6-(3,4-dichlorophenyl)-N-(4-(2-(4-methylpiperazin-1-yl)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine M.p.=119-121° C. 1H NMR 400 MHz (CDCl3) δ 13.02 (br s, 3H), 11.07 (br s, 1H), 8.42-8.35 (m, 1H), 7.97 (s, 1H), 7.74 (d, J=8.2 Hz, 2H), 7.6-7.5 (m, 2H), 7.38-7.34 (m, 1H), 7.28-7.23 (m, 2H), 7.18 (d, J=2.0 Hz, 1H), 7.12-7.07 (m, 1H), 6.9-6.8 (m, 1H), 4.35 (t, J=6.7 Hz, 1H), 3.48 (br s, 8H), 3.3-2.96 (m, 6H), 2.83 (s, 3H). LCMS m/e 545 (M+H).
Workup
- customThis product was synthesized
Sources & evidence
- ORD record
- ord-0f17102ad1344923a0c0894354a3edb7
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357694B2
Reaction notes
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