N-Methylcyclohexylamine → HCID 67427717, compound

HRID 1808050Notes

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][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[ClH:31].[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:20]1[C:19]2[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=2[C:17]2[N:16]=[C:15]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][N:37]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH3:36])=[CH:13][CH:12]=3)[N:24]=[CH:23][C:22]=2[CH2:21]1

Participants

Reactant 2

HCID 7514N-Methylcyclohexylamine

HCID 72305892HCID 72305892, compound

Product 1

HCID 67427717HCID 67427717, 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-methylcyclohexanamine instead of piperidine to afford 6-(2-chlorophenyl)-N-(4-(2-(cyclohexyl(methyl)amino)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine hydrochloride. 1H-NMR 400 MHz (CDCl3) δ 8.45 (d, J=7.8 Hz, 1H), 8.12 (s, 1H), 7.64 (d, J=8.6 Hz, 2H), 7.46-7.39 (m, 3H), 7.21-7.20 (m, 3H), 7.13 (t, J=7.4 Hz, 1H), 7.02 (d, J=7.4 Hz, 2H), 6.73 (d, J=7.8 Hz, 1H), 4.85 (t, J=2.2 Hz, 1H), 3.22-3.17 (m, 2H), 2.75-2.71 (m, 4H), 2.44-2.42 (m, 1H), 2.36 (s, 3H), 1.84-1.79 (m, 4H), 1.64-1.61 (m, 1H), 1.27-1.21 (m, 4H), 1.15-1.10 (m, 1H). LCMS m/e 523 (M+H).

Workup

customThis product was synthesized

Sources & evidence

ORD record: ord-8f91fce3235c49a381195fef9681a71e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357694B2

Reaction notes

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