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

HRID 717399Notes

Reaction equation

HRID 717399 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([OH:20])=O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.[F:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH2:29][NH:28][CH2:27][CH2:26]2>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([N:28]3[CH2:27][CH2:26][C:25]4[C:30](=[CH:31][CH:32]=[C:23]([F:22])[CH:24]=4)[CH2:29]3)=[O:20])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 450740426-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904114972-(4-Fluorophenyl)quinazoline-4-carboxylic acid

Product 1

HCID 904109832-[[2-(4-Fluorophenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinolineYield 24%

Procedure

Reaction of 2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 6-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 11 (24.0% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.90 and 3.13 (2t, 2H), 3.59 and 4.20 (2t, 2H), 4.51 and 5.10 (2s, 2H), 6.79-7.27 (m, 5H), 7.59-7.66 (m, 1H), 7.95-8.05 (m, 2H), 8.16-8.18 (m, 1H), 8.63-8.69 (m, 2H); 19F (282 MHz, DMSO-d6) δ −109.7, −115.1, −115.6; MS (ESI) m/z 402 ([M+H]+).

Sources & evidence

ORD record
ord-dca793efa5a342f2a4b84dc3fcd2864b
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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