(R,E)-2-((dimethylamino)methylene)-4-(2-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one → (R)-2-(2-(6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenyl)ethanol

HRID 1808081Notes

Reaction equation

HRID 1808081 reaction equation
CN(/[CH:4]=[C:5]1/[C:6](=O)[C:7]2[C:12]([C@H:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[CH2:14]/1)=[CH:11][CH:10]=[CH:9][CH:8]=2)C.[OH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33]([NH2:35])=[NH:34]>>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C@H:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]2[N:35]=[C:33]([NH:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH2:25][CH2:24][OH:23])[N:34]=[CH:4][C:5]=2[CH2:14]1

Participants

3

Reactant 2

HCID 59490038(R,E)-2-((dimethylamino)methylene)-4-(2-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-oneHCID 178512472HCID 178512472, compound

Product 1

HCID 59489965(R)-2-(2-(6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenyl)ethanol

Procedure

This was synthesized by using general procedure 6 except that (R,E)-2-((dimethylamino)methylene)-4-(2-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one reacted with 1-(2-(2-hydroxyethyl)phenyl)guanidine to give (R)-2-(2-(6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenyl)ethanol. M.p.=162-163° C. 1H NMR 400 MHz (DMSO-d6) δ 9.05 (s, 1 H), 8.23-8.21 (m, 2 H), 7.81-7.79 (d, 1 H), 7.46-7.43 (m, 2 H), 7.30-7.22 (m, 4 H), 7.06-7.02 (m, 3 H), 6.82-6.77 (m, 1 H), 5.21 (t, J=4.4 Hz, 1 H), 4.65 (t, J=6.8 Hz, 1 H), 3.70-3.66 (m, 2 H), 3.19-3.04 (m, 2 H), 2.18 (t, J=6.0 Hz, 2 H). LCMS m/e 412 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-05cebd61725b401b9a61c31fbeac13bc
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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