1-(2-Methoxyethyl)piperazine → HCID 59490024, compound

HRID 1808049Notes

Reaction equation

HRID 1808049 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]([F:31])=[C:27]([F: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][O:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>>[F: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:44]5[CH2:45][CH2:46][N:41]([CH2:40][CH2:39][O:38][CH3:37])[CH2:42][CH2:43]5)=[CH:13][CH:12]=4)[N:24]=[CH:23][C:22]=3[CH2:21]2)[CH:30]=[CH:29][C:28]=1[F:31]

Participants

3

Reactant 2

HCID 27346381-(2-Methoxyethyl)piperazineHCID 72305897HCID 72305897, compound

Product 1

HCID 59490024HCID 59490024, compound

Procedure

This product was synthesized as described in general procedure 2 except 4-(6-(3,4-difluorophenyl)-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 instead of piperidine to afford 6-(3,4-difluorophenyl)-N-(4-(2-(4-(2-methoxyethyl)piperazin-1-yl)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine. M.p.=267-270° C. 1H NMR 400 MHz (DMSO-d6) δ 11.13 (s, 1H), 9.68 (s, 1H), 8.34 (s, 1H), 8.29 (d, J=6.8 Hz, 1H), 7.79 (d, J=8.0 Hz, 2H), 7.55-7.44 (m, 2H), 7.37-7.20 (m, 4H), 7.08 (d, J=5.2 Hz, 1H), 6.92-6.85 (br, 1H), 4.43 (t, J=6.4 Hz, 1H), 3.90-3.10 (m, 17H), 3.19-3.12 (m, 2H), 3.08-3.00 (m, 2H). LCMS m/e 557 (M+1).

Workup

  1. customThis product was synthesized

Sources & evidence

ORD record
ord-805cbda392e5479188b97cdb9fda7195
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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