N-Methylcyclohexylamine → HCID 67541172, compound

HRID 1808047Notes

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][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[ClH:31].[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:20]2[C:19]3[CH:32]=[CH:33][CH:34]=[CH:35][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:37]([CH:38]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]5)[CH3:36])=[CH:9][CH:10]=4)[N:24]=[CH:23][C:22]=3[CH2:21]2)=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 7514N-Methylcyclohexylamine

HCID 72305904HCID 72305904, compound

Product 1

HCID 67541172HCID 67541172, 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-methylcyclohexanamine was used instead of piperidine to afford 6-(4-chlorophenyl)-N-(4-(2-(cyclohexyl(methyl)amino)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine hydrochloride. M.p.=157-163° C. 1H NMR 400 MHz (DMSO) δ 9.94 (bs, 1H), 9.61 (s, 1H), 8.34-8.29 (m, 2H), 7.81 (d, J=8.8 Hz, 2H), 7.54-7.45 (m, 2H), 7.35-7.31 (m, 2H), 7.26 (d, J=8.4 Hz, 2H), 7.16-7.09 (m, 3H), 4.44 (t, J=6.4 Hz, 1H), 3.40-3.07 (m, 4H), 3.02-2.95 (m, 2H), 2.75 (d, J=4.8 Hz, 3H), 2.08-1.98 (m, 2H), 1.84-1.78 (m, 2H), 1.63-1.06 (m, 7H). LCMS m/e 523 (M+H).

Workup

customThis product was synthesized

Sources & evidence

ORD record: ord-aec1f92da69f490b939245ed63153fdf
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357694B2

Reaction notes

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