5-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[[6,7-Dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717483Notes

Reaction equation

HRID 717483 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]=[CH:36][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][CH:36]=[CH:37][C:28]=2[O:27][CH3:26])[CH2:33]1)=[O:23]

Participants

3

Reactant 2

HCID 139482505-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904107066,7-Dimethoxy-2-(4-fluorophenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862686062-[[6,7-Dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinolineYield 20.2%

Procedure

Reaction of 6,7-dimethoxy-2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 5-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 110 (20.2% yield). 1H NMR (400 MHz, DMSO-d6) δ 2.67 and 2.92 (2t, 2H), 3.51-4.09 (m, 11H), 4.47 and 4.98 (2s, 2H), 6.47-7.28 (m, 4H), 7.38-7.42 (m, 1H), 7.51-7.55 (2s, 1H), 7.59-7.63 (m, 1H), 8.15-8.20 (m, 1H), 8.30-8.35 (m, 1H); 19F (376 MHz, DMSO-d6) 6-113.0; MS (ESI) m/z 474 ([M+H]+).

Sources & evidence

ORD record
ord-ae7f3b7d75494b2f87d7e9e91902eb07
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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