1,2,3,4-Tetrahydroisoquinolin-5-ol hydrochloride → 2-[[2-(3,4,5-Trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline

Participants

Role	Name	HCID	Charge
Reactant	1,2,3,4-Tetrahydroisoquinolin-5-ol hydrochloride	HCID 13948252	—
Reactant	2-(3,4,5-Trimethoxyphenyl)quinazoline-4-carboxylic acid	HCID 90410314	—
Product	2-[[2-(3,4,5-Trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline	HCID 86267575	18.8%

Reaction Steps

Reaction of 2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 5-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 93 (18.8% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.74 and 2.87 (2t, 2H), 3.54 and 4.05 (2t, 2H), 3.76-3.78 (2s, 3H), 3.86 and 3.92 (2s, 6H), 4.46 and 4.96 (2s, 2H), 6.30-7.08 (m, 3H), 7.64-8.17 (m, 6H), 9.50 and 9.53 (2s, 1H); MS (ESI) m/z 472 ([M+H]+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193707B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-9f00885424d84a69b718d413077890db
Source note	uspto-grants-2015_11