6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[[6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717490

Reaction equation

HRID 717490 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)[N:7]=[C:6]2[C:27](O)=[O:28].Cl.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[CH2:39][NH:38][CH2:37][CH2:36]2>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)[N:7]=[C:6]2[C:27]([N:38]1[CH2:37][CH2:36][C:35]2[C:40](=[CH:41][CH:42]=[C:33]([O:32][CH3:31])[CH:34]=2)[CH2:39]1)=[O:28]

Participants

3

Reactant 2

HCID 29203356-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904106406,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862688192-[[6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolineYield 32.7%

Procedure

Reaction of 6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 117 (32.7% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.89 and 3.05 (2t, 2H), 3.48-4.05 (m, 20H), 4.40 and 4.92 (2s, 2H), 6.65-7.26 (m, 4H), 7.47 and 7.50 (2s, 1H), 7.78 and 7.83 (2s, 2H); MS (ESI) m/z 546 ([M+H]+).

Sources & evidence

ORD record
ord-2914e288840c45328de723f0f3bc3ae7
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Linked notes

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