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

HRID 717412Notes

Reaction equation

HRID 717412 reaction equation
[O:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[C:17]([C:19](O)=[O:20])[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.[OH:23][C:24]1[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]2[C:25]=1[CH2:26][CH2:27][NH:28][CH2:29]2>>[O:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[C:17]([C:19]([N:28]3[CH2:27][CH2:26][C:25]4[C:30](=[CH:31][CH:32]=[C:33]([CH3:34])[C:24]=4[OH:23])[CH2:29]3)=[O:20])[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 904112275-Hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 862694252-[[2-(4-Methoxylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinolineYield 22%

Procedure

Reaction of 2-(4-methoxylphenyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 26 (22% yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 2.25 and 2.28 (2s, 3H), 2.81 and 3.04 (2t, 2H), 3.60 and 4.22 (2t, 2H), 3.93 (s, 3H), 4.49 and 5.09 (2s, 2H), 6.34-6.93 (m, 2H), 7.05-7.09 (m, 3H), 7.56-7.64 (m, 1H), 7.94-8.04 (m, 2H), 8.32-8.33 (m, 1H), 8.64-8.70 (m, 2H); MS (ESI) m/z 426 ([M+H]+).

Sources & evidence

ORD record
ord-98a8b61436ab4ad680dbd705b6de2073
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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