2-(3-(Trifluoromethyl)phenyl)quinazoline-4-carboxylic acid → 2-[[2-(3-(Trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline

HRID 717434Notes

Reaction equation

HRID 717434 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[N:18]=[C:17]([C:19](O)=[O:20])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[OH:25][C:26]1[C:35]([N:36]([CH3:38])[CH3:37])=[CH:34][CH:33]=[C:32]2[C:27]=1[CH2:28][CH2:29][NH:30][CH2:31]2>>[F:22][C:2]([F:23])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[N:18]=[C:17]([C:19]([N:30]3[CH2:29][CH2:28][C:27]4[C:32](=[CH:33][CH:34]=[C:35]([N:36]([CH3:38])[CH3:37])[C:26]=4[OH:25])[CH2:31]3)=[O:20])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 904106572-(3-(Trifluoromethyl)phenyl)quinazoline-4-carboxylic acidHCID 904113285-Hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 862698352-[[2-(3-(Trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinolineYield 5%

Procedure

Reaction of 2-(3-(trifluoromethyl)phenyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 55 (5% yield) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 2.71 and 2.77 (2s, 6H), 2.85 and 3.11 (2t, 2H), 3.59 and 4.22 (2t, 2H), 4.49 and 5.11 (2s, 2H), 6.36 and 6.86 (2d, 1H), 6.99-7.17 (m, 2H), 7.62-7.70 (m, 2H), 7.77-7.80 (m, 1H), 7.96-8.07 (m, 2H), 8.16-8.21 (m, 1H), 8.82-8.96 (m, 2H); MS (ESI) m/z 493 ([M+H]+).

Sources & evidence

ORD record
ord-d1f138afab4e4cddae9034528761af16
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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