5,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → HCID 86267367, compound

HRID 717451Notes

Reaction equation

HRID 717451 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[N:16]=[C:15]([C:17]([OH:19])=O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)(=[O:3])[CH3:2].Cl.[CH3:21][O:22][C:23]1[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[C:29]2[C:24]=1[CH2:25][CH2:26][NH:27][CH2:28]2>>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[N:16]=[C:15]([C:17]([N:27]2[CH2:26][CH2:25][C:24]3[C:29](=[CH:30][CH:31]=[C:32]([O:33][CH3:34])[C:23]=3[O:22][CH3:21])[CH2:28]2)=[O:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 717574045,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 90411145HCID 90411145, compound

Product 1

HCID 86267367HCID 86267367, compoundYield 17%

Procedure

Reaction of 2-(2-(acetamido)ethyl)quinazoline-4-carboxylic acid with 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 76 (17% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.74-1.75 (m, 3H), 2.69 and 2.95 (2t, 2H), 3.14-3.19 (m, 2H), 3.45 and 3.99 (2t, 2H), 3.57-3.61 (m, 2H), 3.74-3.80 (3s, 6H), 4.36 and 4.89 (2s, 2H), 6.64 and 6.99 (2d, 1H), 6.82 and 7.05 (2d, 1H), 7.67-7.75 (m, 1H), 7.85-7.94 (m, 2H), 8.02-8.06 (m, 2H); MS (ESI) m/z 435 ([M+H]+).

Sources & evidence

ORD record
ord-dde3b99425e740b8bd62b28d693526b9
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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