6-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[[6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline

HRID 717493Notes

Reaction equation

HRID 717493 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.[F:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH2:38][NH:37][CH2:36][CH2:35]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:37]1[CH2:36][CH2:35][C:34]2[C:39](=[CH:40][CH:41]=[C:32]([F:31])[CH:33]=2)[CH2:38]1)=[O:29]

Participants

3

Reactant 2

HCID 450740426-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904106406,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862686042-[[6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinolineYield 56.2%

Procedure

Reaction of 6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 6-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 120 (56.2% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.93 and 3.09 (2t, 2H), 3.51-4.05 (m, 17H), 4.47 and 4.98 (2s, 2H), 6.91-7.42 (m, 4H), 7.48 and 7.51 (2s, 1H), 7.78 and 7.83 (2s, 2H); MS (ESI) m/z 534 ([M+H]+).

Sources & evidence

ORD record
ord-8cdbe5b199ad44d1ae07061f167b620e
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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