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

HRID 717476Notes

Reaction equation

HRID 717476 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]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)[N:6]=[C:5]2[C:24](O)=[O:25].Cl.[OH:28][C:29]1[C:38]([O:39][CH3:40])=[CH:37][CH:36]=[C:35]2[C:30]=1[CH2:31][CH2:32][NH:33][CH2:34]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:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)[N:6]=[C:5]2[C:24]([N:33]1[CH2:32][CH2:31][C:30]2[C:35](=[CH:36][CH:37]=[C:38]([O:39][CH3:40])[C:29]=2[OH:28])[CH2:34]1)=[O:25]

Participants

3

Reactant 2

HCID 904103076-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acidHCID 904111806-Methoxy-1,2,3,4-tetrahydroisoquinolin-5-ol hydrochloride

Product 1

HCID 862677852-[[6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinolineYield 18.6%

Procedure

Reaction of 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 103 (18.6% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.82 and 2.91 (2t, 2H), 3.56 and 4.02 (2t, 2H), 3.74-3.80 (m, 6H), 3.86 and 3.91 (2s, 6H), 4.45 and 4.90 (2s, 2H), 6.33-6.91 (m, 2H), 7.62-7.86 (m, 3H), 8.00-8.06 (m, 1H), 8.21-8.28 (m, 1H), 8.70 and 8.73 (2s, 1H); MS (ESI) m/z 520 ([M+H]+).

Sources & evidence

ORD record
ord-5ce0b27c5cbd497b817fd70aa0ee3809
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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