1-(2-Methoxyethyl)piperazine → HCID 67426012, compound

HRID 1808048Notes

Reaction equation

HRID 1808048 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])=[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][O:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>>[ClH:31].[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:20]2[C:19]3[CH:32]=[CH:33][CH:34]=[CH:35][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:43]5[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][O:37][CH3:36])[CH2:41][CH2:42]5)=[CH:13][CH:12]=4)[N:24]=[CH:23][C:22]=3[CH2:21]2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 27346381-(2-Methoxyethyl)piperazineHCID 72305904HCID 72305904, compound

Product 1

HCID 67426012HCID 67426012, compound

Procedure

This product was synthesized as described in general procedure 2 except 4-(6-(4-chlorophenyl)-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 1-(2-methoxyethyl)piperazine was used instead of piperidine to afford 6-(4-chlorophenyl)-N-(4-(2-(4-(2-methoxyethyl)piperazin-1-yl)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine hydrochloride. M.p.=204-214° C. 1H NMR 400 MHz (DMSO) δ 12.03-11.35 (m, 2H), 9.64 (s, 1H), 8.34-8.29 (m, 2H), 7.82 (d, J=8.4 Hz, 2H), 7.54-7.46 (m, 2H), 7.35-7.31 (m, 2H), 7.25 (d, J=8.0 Hz, 2H), 7.16-7.10 (m, 3H), 4.47-4.41 (m, 1H), 3.90-3.30 (m, 16H), 3.30-3.00 (m, 5H). LCMS m/e 554 (M+H).

Workup

  1. customThis product was synthesized

Sources & evidence

ORD record
ord-a3638df97ba041b2ba7894f4df98e6d0
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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