N-Methylbutylamine → N-(4-(2-(butyl(methyl)amino)ethyl)phenyl)-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine

HRID 1808041Notes

Reaction equation

HRID 1808041 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.CS(OCCC1C=CC=CC=1)(=O)=O.[CH3:50][NH:51][CH2:52][CH2:53][CH2:54][CH3:55]>>[CH2:52]([N:51]([CH3:50])[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)[CH2:53][CH2:54][CH3:55]

Participants

4

Reactant 3

HCID 8068N-MethylbutylamineHCID 146679Methanesulfonic acid, 2-phenylethyl esterHCID 866455874-(6-(3,4-Dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate

Product 1

HCID 59489880N-(4-(2-(butyl(methyl)amino)ethyl)phenyl)-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine

Procedure

This was synthesized by using 4-(6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate instead of 44643-bromophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate and N-methylbutylamine in place of piperidine as described in general procedure 2 to afford N-(4-(2-(butyl(methyl)amino)ethyl)phenyl)-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine 1H NMR 400 MHz (CDCl3) δ 13.14 (s, 1H), 10.31 (br s, 1H), 8.42-8.36 (m, 1H), 8.0 (s, 1H), 7.74 (d, J=8.6 Hz, 2H), 7.62-7.5 (m, 2H), 7.39-7.27 (m, 1H), 7.19 (d, J=1.9 Hz, 1H), 7.09-7.06 (m, 1H), 6.92-6.8 (m, 1H), 4.33 (t, J=6.3 Hz, 1H), 3.58-2.9 (m, 8H), 2.85 (s, 3H), 1.84-1.68 (m, 2H), 1.5-1.35 (m, 2H), 0.98 (t, J=7.4 Hz, 2H). LCMS m/e 531 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-42eb86a876854cb3a16a2cd656addb7f
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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