6,7-Dimethoxy-2-(4-fluorophenyl)quinazoline-4-carboxylic acid → 2-[[6,7-Dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717485Notes

Reaction equation

HRID 717485 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[N:7]=[C:6]2[C:22](O)=[O:23].Cl.[CH3:26][O:27][C:28]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[C:34]2[C:29]=1[CH2:30][CH2:31][NH:32][CH2:33]2>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[N:7]=[C:6]2[C:22]([N:32]1[CH2:31][CH2:30][C:29]2[C:34](=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:28]=2[O:27][CH3:26])[CH2:33]1)=[O:23]

Participants

3

Reactant 2

HCID 904107066,7-Dimethoxy-2-(4-fluorophenyl)quinazoline-4-carboxylic acidHCID 904118065,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 862684062-[[6,7-Dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 49.2%

Procedure

Reaction of 6,7-dimethoxy-2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 112 (49.2% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.76 and 3.02 (2t, 2H), 3.45-4.08 (m, 14H), 4.24 and 4.78 (2s, 2H), 6.34-6.52 (m, 2H), 6.96 and 7.14 (2s, 1H), 7.36-7.41 (m, 1H), 7.52-7.65 (m, 2H), 8.11-8.21 (m, 1H), 8.28-8.35 (m, 1H); MS (ESI) m/z 504 ([M+H]+).

Sources & evidence

ORD record
ord-237673ae5c0d4ba598800bc51fd1e516
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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