5-Aminoquinoline → 9-Methoxy-2-(quinolin-5-ylamino)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

HRID 1784079Notes

Reaction equation

HRID 1784079 reaction equation
Cl[C:2]1[CH:17]=[C:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[C:4](=[O:18])[N:3]=1)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3.[NH2:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[N:25]2>>[CH3:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:6]1=[CH:17][C:2]([NH:19][C:20]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:21]=3[CH:22]=[CH:23][CH:24]=[N:25]4)=[N:3][C:4](=[O:18])[N:5]1[CH2:14][CH2:13]2

Participants

3

Reactant 2

HCID 119115-AminoquinolineHCID 575910932-chloro-9-methoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 113721389-Methoxy-2-(quinolin-5-ylamino)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

Procedure

The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 5-amino-quinoline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.68 (br, 1H), 8.93 (dd, 1H), 8.47 (d, 1H), 7.89 (2H), 7.79 (t, 1H), 7.70 (d, 1H), 7.57 (dd, 1H), 7.03-6.97 (2H), 6.49 (br, 1H), 3.97 (t, 2H), 3.84 (s, 3H) and 2.97 (t, 2H); MS (ESI) (M+H)+ 371.

Sources & evidence

ORD record
ord-ffc01c1b489b4d53a6148a0d3a600342
Source dataset
uspto-grants-2009_03
Patent number
US07501512B2

Reaction notes

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