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

HRID 717489Notes

Reaction equation

HRID 717489 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:42]=[CH:41][CH:40]=[C:39]2[C:34]=1[CH2:35][CH2:36][NH:37][CH2:38]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:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=1)[N:7]=[C:6]2[C:27]([N:37]1[CH2:36][CH2:35][C:34]2[C:39](=[CH:40][CH:41]=[CH:42][C:33]=2[O:32][CH3:31])[CH2:38]1)=[O:28]

Participants

3

Reactant 2

HCID 139482505-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904106406,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862688212-[[6,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinolineYield 41.6%

Procedure

Reaction of 6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 5-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 116 (41.6% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.84 and 2.90 (2t, 2H), 3.52-4.09 (m, 20H), 4.45 and 4.96 (2s, 2H), 6.45-7.26 (m, 4H), 7.45 and 7.49 (2s, 1H), 7.76 and 7.82 (2s, 2H); MS (ESI) m/z 546 ([M+H]+).

Sources & evidence

ORD record
ord-69139a6b390645b282c6132173a61aa6
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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