1,2,3,4-Tetrahydroisoquinolin-5-ol hydrochloride → 2-[[6-Fluoro-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	6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid	HCID 90410307	—
Product	2-[[6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline	HCID 86267787	15.4%

Reaction Steps

Reaction of 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 5-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 107 (15.4% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.80 and 2.89 (2t, 2H), 3.59 and 4.07 (2t, 2H), 3.77-3.3.80 (m, 3H), 3.87 and 3.92 (2s, 6H), 4.51 and 4.95 (2s, 2H), 6.35-6.79 (m, 2H), 6.89-7.11 (m, 1H), 7.64-7.85 (m, 3H), 8.00-8.09 (m, 1H), 8.22-8.29 (m, 1H), 9.51 and 9.53 (2s, 1H); MS (ESI) m/z 490 ([M+H]+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193707B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-0611ec3546794b389c7296b1840d6181
Source note	uspto-grants-2015_11