6-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[[2-(3,4,5-Trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline

HRID 717467Notes

Reaction equation

HRID 717467 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:22]=[C:21]([C:23](O)=[O:24])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl.[F:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH2:34][NH:33][CH2:32][CH2:31]2>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:22]=[C:21]([C:23]([N:33]3[CH2:32][CH2:31][C:30]4[C:35](=[CH:36][CH:37]=[C:28]([F:27])[CH:29]=4)[CH2:34]3)=[O:24])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 450740426-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904103142-(3,4,5-Trimethoxyphenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862682072-[[2-(3,4,5-Trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinolineYield 63.4%

Procedure

Reaction of 2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 6-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 94 (63.4% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.88 and 3.07 (2t, 2H), 3.54 and 4.05 (2t, 2H), 3.76-3.78 (2s, 3H), 3.87 and 3.92 (2s, 6H), 4.50 and 5.00 (2s, 2H), 6.93-7.14 (m, 2H), 7.38-7.91 (m, 4H), 7.99-8.18 (m, 3H); MS (ESI) m/z 474 ([M+H]+).

Sources & evidence

ORD record
ord-903609a8472543099e48fb81539ee1d3
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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