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

HRID 717397Notes

Reaction equation

HRID 717397 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18](O)=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.[OH:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH2:25][CH2:26][NH:27][CH2:28]2>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:17]=[C:16]([C:18]([N:27]3[CH2:26][CH2:25][C:24]4[C:29](=[CH:30][CH:31]=[CH:32][C:23]=4[OH:22])[CH2:28]3)=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 139482521,2,3,4-Tetrahydroisoquinolin-5-ol hydrochlorideHCID 904114972-(4-Fluorophenyl)quinazoline-4-carboxylic acid

Product 1

HCID 904111142-[[2-(4-Fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinolineYield 24.2%

Procedure

Reaction of 2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 5-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 9 (24.2% yield): 1H NMR (300 MHz, DMSO-d6) δ 2.60 and 2.87 (2t, 2H), 3.51 and 4.07 (2t, 2H), 4.45 and 4.96 (2s, 2H), 6.32-6.79 (m, 2H), 6.88 and 7.08 (2t, 1H), 7.37-7.44 (m, 2H), 7.70-7.79 (m, 1H), 7.88-7.99 (2d, 1H), 8.07-8.18 (m, 2H), 8.53-8.62 (m, 2H), 9.50 and 9.55 (2s, 1H); 19F (282 MHz, DMSO-d6) δ −110.0; MS (ESI) m/z 400 ([M+H]+).

Sources & evidence

ORD record
ord-75469c8f260c480fba635dd0a267aaab
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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