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

HRID 717475Notes

Reaction equation

HRID 717475 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]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[N:6]=[C:5]2[C:19]([OH:21])=O.Cl.[F:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH2:30][NH:29][CH2:28][CH2:27]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]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[N:6]=[C:5]2[C:19]([N:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][CH:33]=[C:24]([F:23])[CH:25]=2)[CH2:30]1)=[O:21]

Participants

3

Reactant 2

HCID 450740426-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904107136-Fluoro-2-(4-fluorophenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862682112-[[6-Fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinolineYield 26.7%

Procedure

Reaction of 6-fluoro-2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 6-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 102 (26.7% yield). 1H NMR (400 MHz, CDCl3) δ 2.95 and 3.13 (2t, 2H), 3.64 and 4.20 (2t, 2H), 4.56 and 5.09 (2s, 2H), 6.82-7.28 (m, 4H), 7.50-7.54 (m, 1H), 7.70-7.77 (m, 2H), 8.17-8.21 (m, 1H), 8.28-8.35 (m 1H), 8.40-8.44 (m, 1H); 19F (376 MHz, DMSO-d6) δ −108.2, −112.8, −115.0, −115.6; MS (ESI) m/z 420 ([M+H]+).

Sources & evidence

ORD record
ord-05a5d18a524e4d9a9ebd4178a48c70a3
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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