5,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → HCID 86269837, compound

HRID 717437Notes

Reaction equation

HRID 717437 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:18]=[C:17]([C:19](O)=[O:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.Cl.[CH3:23][O:24][C:25]1[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[C:31]2[C:26]=1[CH2:27][CH2:28][NH:29][CH2:30]2>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:18]=[C:17]([C:19]([N:29]2[CH2:28][CH2:27][C:26]3[C:31](=[CH:32][CH:33]=[C:34]([O:35][CH3:36])[C:25]=3[O:24][CH3:23])[CH2:30]2)=[O:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

3

Reactant 2

HCID 717574045,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 90410716HCID 90410716, compound

Product 1

HCID 86269837HCID 86269837, compoundYield 12%

Procedure

Reaction of 2-(2,4-difluorophenyl)quinazoline-4-carboxylic acid with 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 59 (12% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.72 and 2.97 (2t, 2H), 3.50 and 4.01 (2t, 2H), 3.68-3.81 (m, 6H), 4.42 and 4.92 (2s, 2H), 6.64 and 7.00 (2d, 1H), 6.82 and 7.07 (2d, 1H), 7.28-7.49 (m, 2H), 7.75-7.84 (m, 1H), 7.93-8.10 (m, 1H), 8.13-8.26 (m, 3H); MS (ESI) m/z 462 ([M+H]+).

Sources & evidence

ORD record
ord-a0c9218d548a4dfcbc2481095c98e206
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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