5,6-Dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide → 2-[[2-(3-Methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline

HRID 717429Notes

Reaction equation

HRID 717429 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1)[CH3:2].Br.[OH:23][C:24]1[C:33]([OH: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:4]=[C:5]([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]([OH: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:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 861765835,6-Dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromideHCID 904102332-(3-Methoxylphenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862696362-[[2-(3-Methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinolineYield 9%

Procedure

Reaction of 2-(3-methoxylphenyl)quinazoline-4-carboxylic acid with 5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide gave compound 48 (9% yield) as brown oil. 1H NMR (300 MHz, CD3OD) δ 2.83 and 3.05 (2t, 2H), 3.55 and 4.14 (2t, 2H), 3.87-3.92 (2s, 3H), 4.40 and 4.98 (2s, 2H), 6.15 and 6.64 (2d, 1H), 6.54 and 6.75 (2d, 1H), 7.08-7.12 (m, 1H), 7.41-7.47 (m, 1H), 7.69-7.74 (m, 1H), 7.88-8.21 (m, 5H); MS (ESI) m/z 428 ([M+H]+).

Sources & evidence

ORD record
ord-06e0b857df164fadac734ecf269b135b
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

Loading…