N-Methylbutylamine → HCID 67541864, compound

HRID 1808067Notes

Reaction equation

HRID 1808067 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][CH2:39][CH2:40][CH2:41][CH3:42]>C(N(CC)CC)C>[ClH:31].[CH2:39]([N:38]([CH3:37])[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)[CH2:40][CH2:41][CH3:42]

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 86645590HCID 86645590, compound

Product 1

HCID 67541864HCID 67541864, 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-methylbutan-1-amine and triethylamine as described in general procedure 2 to afford the desired product. M.p.=135-145° C. 1H NMR 400 MHz (DMSO-d6) δ 10.52 (s, 2 H), 9.70 (s, 1 H), 8.33-8.28 (m, 2 H), 7.78-7.76 (m, 2 H), 7.51-7.42 (m, 4 H), 7.24-7.22 (d, 2 H), 7.11-7.09 (m, 1 H), 7.02-7.00 (m, 1 H), 4.46 (t, J=6.4 Hz, 1 H), 3.28-3.11 (m, 5 H), 3.00-2.96 (m, 3 H), 2.75 (d, 3 H), 1.67-1.61 (m, 2 H), 1.33-1.27 (m, 2 H), 0.89 (t, J=7.6 Hz, 3 H). LCMS m/e 531 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-d4f1fdd83307414287113ead3ff5ba51
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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