N-Methylcyclohexylamine → HCID 46834395, compound

HRID 1808066Notes

Reaction equation

HRID 1808066 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]([F: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>C(N(CC)CC)C>[CH:38]1([N:37]([CH3:36])[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]([F:31])=[CH:27][CH:26]=5)[C:19]5[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=5[C:17]=4[N:16]=3)=[CH:10][CH:9]=2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 59490197HCID 59490197, compound

Product 1

HCID 46834395HCID 46834395, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This was synthesized by using (S)-4-(6-(4-fluorophenyl)-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.=160-162° C. 1H NMR (DMSO-d6) 400 MHz δ 10.37 (brs, 1H), 9.68 (s, 1H), 8.32-8.36 (m, 2H), 7.80 (d, J=7.8 Hz, 2H), 7.50-7.52 (m, 2H), 7.26 (d, J=8.2 Hz, 2H), 7.10-7.17 (m, 4H), 4.43 (t, J=6.6 Hz, 1H), 3.27-3.30 (m, 5H), 3.01-3.13 (m, 2H), 2.73 (d, J=4.6 Hz, 3H), 2.03-2.09 (m, 2H), 1.99 (s, 1H), 1.81 (d, J=12.1 Hz, 2H), 1.61 (d, J=12.5 Hz, 1H), 1.40-1.44 (m, 3H), 1.27-1.32 (m, 3H), 1.09-1.17 (m, 2H). LCMS m/e 507 [M+H].

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-7eda85f6afe64255be3d3db8af750f2c
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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