5,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → HCID 86270401, compound

HRID 717448Notes

Reaction equation

HRID 717448 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:16]=[C:15]([C:17]([OH:19])=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[N:3][CH:2]=1.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>>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:16]=[C:15]([C:17]([N:27]3[CH2:26][CH2:25][C:24]4[C:29](=[CH:30][CH:31]=[C:32]([O:33][CH3:34])[C:23]=4[O:22][CH3:21])[CH2:28]3)=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[N:3][CH:2]=1

Participants

3

Reactant 2

HCID 717574045,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904109312-(Pyrimidin-4-yl)quinazoline-4-carboxylic acid

Product 1

HCID 86270401HCID 86270401, compoundYield 17%

Procedure

Reaction of 2-(4-pyrimidinyl)quinazoline-4-carboxylic acid with 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 72 (17% yield) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 2.86 and 3.13 (2t, 2H), 3.54 and 4.17 (2t, 2H), 3.81-3.90 (m, 6H), 4.43 and 5.06 (2s, 2H), 6.51 and 6.91 (2d, 1H), 6.71 and 7.01 (2d, 1H), 7.74-7.81 (m, 2H), 8.04-8.13 (m, 2H), 8.39-8.41 (2s, 1H), 8.65-8.70 (m, 1H), 9.04-9.06 (m, 1H), 9.57 (s, 1H); MS (ESI) m/z 428 ([M+H]+).

Sources & evidence

ORD record
ord-e1d92976117f44abb864b9da863d9820
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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