N-Methylcyclohexylamine → HCID 67540972, compound

HRID 1808068Notes

Reaction equation

HRID 1808068 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][C@@H: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.[CH3:37][NH:38][CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>C(N(CC)CC)C>[ClH:31].[CH:39]1([N:38]([CH3:37])[CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:24]=[CH:23][C:22]4[CH2:21][C@@H:20]([C:25]5[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=5)[C:19]5[CH:33]=[CH:34][CH:35]=[CH:36][C:18]=5[C:17]=4[N:16]=3)=[CH:10][CH:9]=2)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 86645590HCID 86645590, compound

Product 1

HCID 67540972HCID 67540972, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This was synthesized by using (S)-4-(6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate, N-methylcyclohexanamine and triethylamine as described in general procedure 2 to afford the desired product. M.p.=175-185° C. 1H NMR 400 MHz (DMSO-d6) δ 10.54 (s, 1 H), 9.71 (s, 1 H), 8.33-8.28 (m, 2 H), 7.78-7.76 (m, 2 H), 7.51-7.42 (m, 3 H), 7.25-7.23 (m, 2 H), 7.11-7.10 (d, 1 H), 7.02-7.00 (m, 1 H), 4.46 (t, J=6.8 Hz, 1 H), 3.28-3.21 (m, 4 H), 3.00-2.98 (m, 2 H), 2.71-2.69 (d, 3 H), 2.09-1.96 (m, 2 H), 1.79 (d, J=12 Hz, 2 H), 1.59 (d, J=12.8 Hz, 2 H). 1.44-1.38 (m, 2 H), 1.26-1.06 (m, 4 H). LCMS m/e 557 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-f32360d25e084d35925e6ab994d315c9
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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