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

HRID 717487Notes

Reaction equation

HRID 717487 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.[F:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[CH2:33][NH:32][CH2:31][CH2:30]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:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[N:7]=[C:6]2[C:22]([N:32]1[CH2:31][CH2:30][C:29]2[C:34](=[CH:35][CH:36]=[C:27]([F:26])[CH:28]=2)[CH2:33]1)=[O:23]

Participants

3

Reactant 2

HCID 450740426-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904107066,7-Dimethoxy-2-(4-fluorophenyl)quinazoline-4-carboxylic acid

Product 1

HCID 904108652-[[6,7-Dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinolineYield 17.9%

Procedure

Reaction of 6,7-dimethoxy-2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 6-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 114 (17.9% yield). 1H NMR (400 MHz, DMSO-d6) δ 2.84 and 3.09 (2t, 2H), 3.50-4.06 (m, 8H), 4.47 and 4.98 (2s, 2H), 6.94-7.43 (m, 5H), 7.52-7.55 (2s, 1H), 7.59-7.65 (m, 1H), 8.13-8.21 (m, 1H), 8.30-8.35 (m, 1H); 19F (376 MHz, DMSO-d6) δ −113.0, −116.1, −116.3; MS (ESI) m/z 462 ([M+H]+).

Sources & evidence

ORD record
ord-4fc69d0806e34798946a74d8a9f19b10
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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