1-(2-Methoxyethyl)piperazine → 6-(3,4-dichlorophenyl)-N-(4-(2-(4-(2-methoxyethyl)piperazin-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][O:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]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:10]=[CH:9][C:8]([CH2:7][CH2:6][N:44]5[CH2:45][CH2:46][N:41]([CH2:40][CH2:39][O:38][CH3:37])[CH2:42][CH2:43]5)=[CH:13][CH:12]=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 1-(2-methoxyethyl piperazine was used instead of piperidine to give 6-(3,4-dichlorophenyl)-N-(4-(2-(4-(2-methoxyethyl)piperazin-1-yl)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine M.p.=121-122° C. 1H NMR 400 MHz (CDCl3) δ 12.75 (br s, 3H), 11.8 (s, 1H), 8.37 (br s, 1H), 7.98 (br s, 1H), 7.76 (br s, 2H), 7.60 (m, 2H), 7.36-7.27 (m, 1H), 7.18 (s, 1H), 7.10 (d, J=7.1 Hz, 1H), 6.88 (d, J=7.9 Hz, 1H), 4.37 (br s,1H), 4.0-3.6 (br s,8H), 3.45-3.0 (m, 8H), 2.72 (s, 3H). LCMS m/e 588 (M+H).
Workup
- customThis product was synthesized
Sources & evidence
- ORD record
- ord-dacea6697a1b40e8bb25c43d7471db01
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357694B2
Reaction notes
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