Guanidine Hydrochloride → (R)-6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine

HRID 1808039Notes

Reaction equation

HRID 1808039 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.Cl.[NH2:24][C:25]([NH2:27])=[NH:26]>>[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:24]=[C:25]([NH2:27])[N:26]=[CH:4][C:5]=2[CH2:14]1

Participants

3

Reactant 2

HCID 5742Guanidine HydrochlorideHCID 59490038(R,E)-2-((dimethylamino)methylene)-4-(2-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 59489790(R)-6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine

Procedure

This was synthesized by using (R,E)-2-((dimethylamino)methylene)-4-(2-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one and guanidine hydrochloride as described in general procedure 1 to afford the desired product as hydrochloride salt. M.p.=154-155° C. 1H NMR 400 MHz (DMSO-d6) δ 8.26-8.24 (m, 1 H), 8.08 (s, 1 H), 7.46-7.39 (m, 2 H), 7.31-7.20 (m, 2 H), 7.05-7.00 (m, 2 H), 6.80-6.76 (m, 1 H), 6.51 (s, 2 H), 4.59 (t, J=6.8 Hz, 1 H), 3.11-3.2.96 (m, 2 H). LCMS m/e 292 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-6caaabcc87c04a4c82c774e4ebbca983
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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