5,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[[2-(4-(Acetamidomethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717444Notes

Reaction equation

HRID 717444 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:21]=[C:20]([C:22](O)=[O:23])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].Cl.[CH3:26][O:27][C:28]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[C:34]2[C:29]=1[CH2:30][CH2:31][NH:32][CH2:33]2>>[C:1]([NH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:21]=[C:20]([C:22]([N:32]3[CH2:31][CH2:30][C:29]4[C:34](=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:28]=4[O:27][CH3:26])[CH2:33]3)=[O:23])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 717574045,6-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 904107082-(4-(Acetamidomethyl)phenyl)quinazoline-4-carboxylic acid

Product 1

HCID 862700232-[[2-(4-(Acetamidomethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 5%

Procedure

Reaction of 2-(4-(acetamidomethyl)phenyl)quinazoline-4-carboxylic acid with 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 67 (5% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.91 (s, 3H), 2.73 and 2.98 (2t, 2H), 3.48 and 4.03 (2t, 2H), 3.69-3.82 (4s, 6H), 4.34-4.36 (m, 2H), 4.41 and 4.93 (2s, 2H), 6.62 and 7.01 (2d, 1H), 6.80 and 7.08 (2d, 1H), 7.42-7.47 (m, 2H), 7.75-8.17 (m, 4H), 8.44-8.51 (m, 3H); MS (ESI) m/z 497 ([M+H]+).

Sources & evidence

ORD record
ord-1ab6840c1ff24eb5be9b581793c2e775
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

Loading…