5-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[[2-(3,4,5-Trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717463Notes

Reaction equation

HRID 717463 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:22]=[C:21]([C:23]([OH:25])=O)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl.[CH3:27][O:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH2:31][CH2:32][NH:33][CH2:34]2>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:22]=[C:21]([C:23]([N:33]3[CH2:32][CH2:31][C:30]4[C:35](=[CH:36][CH:37]=[CH:38][C:29]=4[O:28][CH3:27])[CH2:34]3)=[O:25])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 139482505-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904103142-(3,4,5-Trimethoxyphenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862679912-[[2-(3,4,5-Trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinolineYield 36.3%

Procedure

Reaction of 2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid with 5-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 90 (36.3% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.79 and 2.90 (2t, 2H), 3.56 and 4.08 (2t, 2H), 3.76-3.81 (m, 6H), 3.86 and 3.92 (2s, 6H), 4.50 and 4.99 (2s, 2H), 6.49-7.28 (m, 3H), 7.67-8.18 (m, 6H); MS (ESI) m/z 486 ([M+H]+).

Sources & evidence

ORD record
ord-a6f2184180ba420580ebdebe11af54a6
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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