6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid → 2-[[6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717488Notes

Reaction equation

HRID 717488 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)[N:7]=[C:6]2[C:27]([OH:29])=O.Cl.[OH:31][C:32]1[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[C:38]2[C:33]=1[CH2:34][CH2:35][NH:36][CH2:37]2>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=1)[N:7]=[C:6]2[C:27]([N:36]1[CH2:35][CH2:34][C:33]2[C:38](=[CH:39][CH:40]=[C:41]([O:42][CH3:43])[C:32]=2[OH:31])[CH2:37]1)=[O:29]

Participants

3

Reactant 2

HCID 904106406,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acidHCID 904111806-Methoxy-1,2,3,4-tetrahydroisoquinolin-5-ol hydrochloride

Product 1

HCID 904111422-[[6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinolineYield 13.6%

Procedure

Reaction of 6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 115 (13.6% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.83 and 2.90 (2t, 2H), 3.49-4.05 (m, 20H), 4.37 and 4.90 (2s, 2H), 6.27-7.16 (m, 3H), 7.46 and 7.50 (2s, 1H), 7.78 and 7.84 (2s, 2H), 8.70 and 8.73 (2s, 1H); MS (ESI) m/z 562 ([M+H]+).

Sources & evidence

ORD record
ord-8712cd5330e34bf8bf2b690e17882f6b
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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