N-Methylbutylamine → HCID 67427772, compound

HRID 1808051Notes

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][CH:28]=[CH:27][C:26]=4[Cl:31])[C:19]4[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=4[C:17]=3[N:16]=2)=[CH:10][CH:9]=1)(=O)=O.[CH3:36][NH:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[ClH:31].[CH2:38]([N:37]([CH3:36])[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][CH:28]=[CH:27][C:26]=4[Cl:31])[C:19]4[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=4[C:17]=3[N:16]=2)=[CH:10][CH:9]=1)[CH2:39][CH2:40][CH3:41]

Participants

Reactant 2

HCID 8068N-Methylbutylamine

HCID 72305892HCID 72305892, compound

Product 1

HCID 67427772HCID 67427772, compound

Procedure

This product was synthesized as described in general procedure 2 except 4-(6-(2-chlorophenyl)-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-methylbutan-1-amine instead of piperidine to afford N-(4-(2-(butyl(methyl)amino)ethyl)phenyl)-6-(2-chlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine hydrochloride. 1H-NMR 400 MHz (CDCl3) δ 8.44 (dd, J=7.4, 1.1 Hz, 1H), 8.12 (s, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.46-7.39 (m, 3H), 7.24-7.19 (m, 3H), 7.12 (t, J=7.4 Hz, 1H), 7.04 (d, J=7.4 Hz, 2H), 6.75 (dd, J=7.8, 1.5 Hz, 1H), 4.85 (t, J=2.2 Hz, 1H), 3.18-3.12 (m, 2H), 2.79-2.76 (m, 2H), 2.61-2.59 (m, 2H), 2.41 (t, J=7.4 Hz, 1H), 2.31 (s, 3H), 1.51-1.47 (m, 2H), 1.36-1.30 (m, 2H), 0.93 (t, J=7.4 Hz, 3H). LCMS m/e 498 (M+H).

Workup

customThis product was synthesized

Sources & evidence

ORD record: ord-0667014a6f0f401eb1e3cbd77eb683e8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357694B2

Reaction notes

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