1,2,3,4-Tetrahydroisoquinolin-5-ol hydrochloride → 2-[[6-Fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline

HRID 717474Notes

Reaction equation

HRID 717474 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[N:6]=[C:5]2[C:19](O)=[O:20].Cl.[OH:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH2:26][CH2:27][NH:28][CH2:29]2>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[N:6]=[C:5]2[C:19]([N:28]1[CH2:27][CH2:26][C:25]2[C:30](=[CH:31][CH:32]=[CH:33][C:24]=2[OH:23])[CH2:29]1)=[O:20]

Participants

3

Reactant 2

HCID 139482521,2,3,4-Tetrahydroisoquinolin-5-ol hydrochlorideHCID 904107136-Fluoro-2-(4-fluorophenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862677842-[[6-Fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinolineYield 22.8%

Procedure

Reaction of 6-fluoro-2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 5-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 101 (22.8% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.62 and 2.88 (2t, 2H), 3.54 and 4.05 (2t, 2H), 4.49 and 4.95 (2s, 2H), 6.35-6.79 (m, 2H), 6.85-7.07 (m, 1H), 7.42-7.45 (m, 1H), 7.64-7.80 (m, 2H), 8.04-8.10 (m 1H), 8.15-8.39 (m, 3H), 9.49 and 9.53 (2s, 1H); MS (ESI) m/z 418 ([M+H]+).

Sources & evidence

ORD record
ord-726ebcd0765a45f98939bbaeedde2715
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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