5-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[[6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717477Notes

Reaction equation

HRID 717477 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.[CH3:28][O:29][C:30]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:31]=1[CH2:32][CH2:33][NH:34][CH2:35]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]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[N:6]=[C:5]2[C:24]([N:34]1[CH2:33][CH2:32][C:31]2[C:36](=[CH:37][CH:38]=[CH:39][C:30]=2[O:29][CH3:28])[CH2:35]1)=[O:25]

Participants

3

Reactant 2

HCID 139482505-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904103076-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862684042-[[6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinolineYield 41.1%

Procedure

Reaction of 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 5-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 104 (41.1% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.88 and 3.03 (2t, 2H), 3.55 and 4.02 (2t, 2H), 3.72-3.3.77 (m, 6H), 3.86 and 3.92 (2s, 6H), 4.48 and 4.92 (2s, 2H), 6.63-7.27 (m, 3H), 7.62-7.85 (m, 3H), 7.98-8.07 (m, 1H), 8.23-8.26 (m, 1H); MS (ESI) m/z 504 ([M+H]+).

Sources & evidence

ORD record
ord-9aab9c38d32b48beb5db614ab2cd6bbc
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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