Morpholine → 6-(3,4-dichlorophenyl)-N-(4-(2-morpholinoethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine

HRID 1808043Notes

Reaction equation

HRID 1808043 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][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.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>>[Cl:32][C:27]1[CH:26]=[C:25]([CH:20]2[C:19]3[CH:33]=[CH:34][CH:35]=[CH:36][C:18]=3[C:17]3[N:16]=[C:15]([NH:14][C:11]4[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)=[CH:13][CH:12]=4)[N:24]=[CH:23][C:22]=3[CH2:21]2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 866455874-(6-(3,4-Dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate

Product 1

HCID 594901156-(3,4-dichlorophenyl)-N-(4-(2-morpholinoethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amineYield 55%

Procedure

This product was synthesized as described in general procedure 2 except 4-(6-(3,4-dichlorophenyl)-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 morpholine was used instead of piperidine to afford 6-(3,4-dichlorophenyl)-N-(4-(2-morpholinoethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine in 55% yield. M.p.=180-181° C. 1H NMR 400 MHz (CDCl3) δ 8.45-8.4 (m, 1H), 8.17 (s, 1H), 7.62 (d, J=8.4 Hz, 2H), 7.58-6.85 (m, 6H), 4.18-4.0 (m, 1H), 3.84-3.68 (m, 4H), 3.35-3.18 (m, 1H), 3.18-3.0 (m, 1H), 2.92-2.73 (m, 2H), 2.7-2.45 (m, 6H). LCMS m/e 532 (M+H).

Workup

  1. customThis product was synthesized

Sources & evidence

ORD record
ord-fdff6ed48f4a47e094644bdb6a88db34
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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