N-Methylbutylamine → HCID 67427971, compound

HRID 1808046Notes

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])=[CH:27][CH:26]=4)[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][C:28]([Cl:31])=[CH:27][CH:26]=4)[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 72305904HCID 72305904, compound

Product 1

HCID 67427971HCID 67427971, compound

Procedure

This product was synthesized as described in general procedure 2 except 4-(6-(4-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 was used instead of piperidine to afford N-(4-(2-(butyl(methyl)amino)ethyl)phenyl)-6-(4-chlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine hydrochloride. M.p.=145-150° C. 1H NMR 400 MHz (DMSO) δ 10.33 (bs, 1H), 9.65 (s, 1H), 8.35-8.30 (m, 2H), 7.81 (d, J=8.8 Hz, 2H), 7.54-7.45 (m, 2H), 7.36-7.31 (m, 2H), 7.25 (d, J=8.4 Hz, 2H), 7.16-7.09 (m, 3H), 4.44 (t, J=6.4 Hz, 1H), 3.35-2.95 (m, 8H), 2.79 (d, J=4.8 Hz, 3H), 1.72-1.63 (m, 2H), 1.39-1.30 (m, 2H), 0.92 (t, J=7.2, 3H). LCMS m/e 495 (M+H).

Workup

customThis product was synthesized

Sources & evidence

ORD record: ord-f620c0b9072d41e79adbd34b45723800
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357694B2

Reaction notes

Loading…