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

HRID 1808080Notes

Reaction equation

HRID 1808080 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][C:25]1[CH:26]=[C:27]([NH:31][C:32]([NH2:34])=[NH:33])[CH:28]=[CH:29][CH:30]=1>>[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:34]=[C:32]([NH:31][C:27]3[CH:26]=[C:25]([CH2:24][OH:23])[CH:30]=[CH:29][CH:28]=3)[N:33]=[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 178512491N-[3-(Hydroxymethyl)phenyl]guanidine

Product 1

HCID 59489617(R)-(3-(6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenyl)methanol

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-(3-(hydroxymethyl)phenyl)guanidine to give (R)-(3-(6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenyl)methanol M.p.=158-159° C. 1H NMR 400 MHz (DMSO-d6) δ 9.57 (s, 1 H), 8.41-8.39 (m, 1 H), 8.32 (s, 1 H), 7.92 (s, 1 H), 7.70-7.68 (m, 1 H), 7.53-7.45 (m, 2 H), 7.29-7.21 (m, 3 H), 7.08-7.02 (m, 2 H), 6.91-6.89 (d, 1 H), 6.81-6.77 (m, 1 H), 5.19 (t, J=6.0 Hz, 1 H), 4.67 (t, J=6.8 Hz, 1 H), 4.52 (d, J=5.2 Hz, 2H), 3.22-3.02 (m, 2 H). LCMS m/e 398 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-853fcc74b8d944e7961558c8aa4714d8
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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