2-(4-Fluorophenyl)quinazoline-4-carboxylic acid → 2-[[2-(4-Fluorophenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717396Notes

Reaction equation

HRID 717396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([OH:20])=O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:22][O:23][C:24]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]2[C:25]=1[CH2:26][CH2:27][NH:28][CH2:29]2>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:17]=[C:16]([C:18]([N:28]3[CH2:27][CH2:26][C:25]4[C:30](=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:24]=4[O:23][CH3:22])[CH2:29]3)=[O:20])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 904114972-(4-Fluorophenyl)quinazoline-4-carboxylic acidHCID 904118065,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 904109202-[[2-(4-Fluorophenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 23.5%

Procedure

Reaction of 2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 8 (23.5% yield): 1H NMR (300 MHz, DMSO-d6) δ 2.70 and 3.00 (2m, 2H), 3.48 and 4.03 (2m, 2H), 3.74 and 3.75 (m, 3H), 3.46 and 3.87 (s, 3H), 4.24 and 4.78 (2s, 2H), 6.33-6.51 (m, 2H), 7.38-7.44 (m, 2H), 7.72-7.78 (m, 1H), 7.91-7.99 (m, 1H), 8.07-8.17 (m, 2H), 8.52-8.62 (m, 2H); MS (ESI) m/z 444 ([M+H]+).

Sources & evidence

ORD record
ord-80c0e5378d3d4eba8d18ffafad13dde0
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

Loading…