HCID 90410702, compound → HCID 86267987, compound

HRID 717456Notes

Reaction equation

HRID 717456 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[N:15]=[C:14]([C:16]([OH:18])=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)[N:3]=[CH:2]1.Cl.[OH:20][C:21]1[C:30]([N:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][CH2:24][NH:25][CH2:26]2>>[S:1]1[CH:5]=[C:4]([C:6]2[N:15]=[C:14]([C:16]([N:25]3[CH2:24][CH2:23][C:22]4[C:27](=[CH:28][CH:29]=[C:30]([N:31]([CH3:33])[CH3:32])[C:21]=4[OH:20])[CH2:26]3)=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)[N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 90410702HCID 90410702, compoundHCID 904113285-Hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 86267987HCID 86267987, compoundYield 39%

Procedure

Reaction of 2-(4-thiazolyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 82 (39% yield) as a light yellow solid. 1H NMR (300 MHz, CD3OD) δ 2.63 and 2.67 (2s, 6H), 2.82 and 3.06 (2m, 2H), 3.58 and 4.17 (2t, 2H), 4.46 and 5.03 (2s, 2H), 6.31 and 6.81 (2d, 1H), 6.91 and 7.12 (2d, 1H), 7.69-7.95 (m, 2H), 8.04-8.12 (m, 2H), 8.22-8.28 (m, 1H), 8.63-8.73 (2s, 1H), 9.21-9.23 (m, 1H); MS (ESI) m/z 432 ([M+H]+).

Sources & evidence

ORD record
ord-e736872fcc6a4d09921939ebd4e4a8d2
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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