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

HRID 717432Notes

Reaction equation

HRID 717432 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]([OH:21])=O)[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]([O:36][CH3:37])=[CH:34][CH:33]=[C:32]2[C:27]=1[CH2:28][CH2:29][NH:30][CH2:31]2>>[F:23][C:2]([F:22])([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]([O:36][CH3:37])[C:26]=4[OH:25])[CH2:31]3)=[O:21])[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 904111806-Methoxy-1,2,3,4-tetrahydroisoquinolin-5-ol hydrochloride

Product 1

HCID 862702092-[[2-(3-(Trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinolineYield 18%

Procedure

Reaction of 2-(3-(trifluoromethyl)phenyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 52 (18% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.63 and 2.91 (2t, 2H), 3.51 and 4.04 (2t, 2H), 3.74 and 3.80 (2s, 3H), 4.40 and 4.93 (2s, 2H), 6.31 and 6.77 (2d, 1H), 6.70 and 6.91 (2d, 1H), 7.74-8.01 (m, 4H), 8.10-8.16 (m, 1H), 8.20-8.26 (m, 1H), 8.67 and 8.72 (2s, 1H), 8.73-8.85 (m, 2H); MS (ESI) m/z 480 ([M+H]+).

Sources & evidence

ORD record
ord-ee068aba0e6547859e699fbab8af2103
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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