2-(4-Methoxyphenyl)quinazoline-4-carboxylic acid → 2-[[2-(4-Methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717410Notes

Reaction equation

HRID 717410 reaction equation
[O:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[C:17]([C:19]([OH:21])=O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1)[CH3:2].Cl.[CH3:23][O:24][C:25]1[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[C:31]2[C:26]=1[CH2:27][CH2:28][NH:29][CH2:30]2>>[O:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[C:17]([C:19]([N:29]3[CH2:28][CH2:27][C:26]4[C:31](=[CH:32][CH:33]=[C:34]([O:35][CH3:36])[C:25]=4[O:24][CH3:23])[CH2:30]3)=[O:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 691104172-(4-Methoxyphenyl)quinazoline-4-carboxylic acidHCID 717574045,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 862694262-[[2-(4-Methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 13%

Procedure

Reaction of 2-(4-methoxylphenyl)quinazoline-4-carboxylic acid with 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 24 (13% yield) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 2.72 and 2.98 (2t, 2H), 3.48 and 4.03 (2t, 2H), 3.69-3.87 (5s, 9H), 4.41 and 4.93 (2s, 2H), 6.63 and 7.01 (2d, 1H), 6.80 and 7.08 (2d, 1H), 7.11-7.14 (m, 2H), 7.71-7.74 (m, 1H), 7.83-7.95 (2d, 1H), 8.03-8.10 (m, 2H), 8.45-8.51 (m, 2H); MS (ESI) m/z 456 ([M+H]+).

Sources & evidence

ORD record
ord-252df4da7e5b465a8bf2af17cc33f46f
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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