N-Methylbutylamine → HCID 67541190, compound

HRID 1808078Notes

Reaction equation

HRID 1808078 reaction equation
CS(OCC[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.CN[CH2:39][CH2:40]CC.[CH2:43]([N:45]([CH2:48][CH3:49])[CH2:46][CH3:47])C>>[ClH:31].[CH2:46]([N:45]([CH3:43])[CH2:48][CH2:49][C:9]1[CH:10]=[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:12]=[CH:13][CH:8]=1)[CH2:47][CH2:39][CH3:40]

Participants

4

Reactant 3

HCID 8068N-MethylbutylamineHCID 8471TriethylamineHCID 86645590HCID 86645590, compound

Product 1

HCID 67541190HCID 67541190, compound

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 6 to afford the desired product as hydrochloride salt. M.p.=162-166° C. 1H NMR (DMSO) 400 MHz δ 10.24 (bs, 1H), 9.63 (s, 1H), 8.34-8.29 (m, 2H), 7.79 (bs, 1H), 7.68-7.65 (m, 1H), 7.56-7.45 (m, 3H), 7.43-7.41 (m, 1H), 7.27 (t, J=8.0 Hz, 1H), 7.11 (d, J=7.6 Hz, 1H), 7.04-7.00 (m, 1H), 6.87 (d, J=8 Hz, 1H), 4.46 (t, J=6.4 Hz, 1H), 3.34-3.10 (m, 5H), 3.06-2.96 (m, 3H), 2.79 (t, J=4.8 Hz, 3H) 1.68-1.59 (m, 2H), 1.32-1.24 (m, 2H), 0.87 (t, J=7.6 Hz, 3H). LCMS m/e 531 [M+H]. Calc. for C31H32Cl2N4.1.93 Hydrochloric acid.0.30 Water.0.17 Ethyl Acetate: C, 61.15; H, 5.81; N, 9.00. Found C, 61.15; H, 5.82; N, 9.00.

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-07783d40f9c64906afcf6dfc2ba02a27
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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