HCID 90411062, compound → HCID 86268817, compound

HRID 717440Notes

Reaction equation

HRID 717440 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:20]=[C:19]([C:21]([OH:23])=O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.[OH:25][C:26]1[C:35]([O:36][CH3:37])=[CH:34][CH:33]=[C:32]2[C:27]=1[CH2:28][CH2:29][NH:30][CH2:31]2>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:20]=[C:19]([C:21]([N:30]3[CH2:29][CH2:28][C:27]4[C:32](=[CH:33][CH:34]=[C:35]([O:36][CH3:37])[C:26]=4[OH:25])[CH2:31]3)=[O:23])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 90411062HCID 90411062, compoundHCID 904111806-Methoxy-1,2,3,4-tetrahydroisoquinolin-5-ol hydrochloride

Product 1

HCID 86268817HCID 86268817, compoundYield 9%

Procedure

Reaction of 2-(4-acetamidophenyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 62 (9% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.10 (s, 3H), 2.63 and 2.89 (2t, 2H), 3.47 and 4.03 (2t, 2H), 3.74 and 3.80 (2s, 3H), 4.38 and 4.91 (2s, 2H), 6.32 and 6.77 (2d, 1H), 6.70 and 6.91 (2d, 1H), 7.64-7.93 (m, 4H), 8.03-8.13 (m, 2H), 8.41-8.49 (m, 2H), 8.69 and 8.74 (2s, 1H), 10.23 (s, 1H); MS (ESI) m/z 469 ([M+H]+).

Sources & evidence

ORD record
ord-cc450931d2014d44adf894c3f12fe231
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

Loading…