Hydrochloric Acid → 9-Methoxy-2-(2-pyrrolidin-1-yl-ethylamino)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

HRID 1784083Notes

Reaction equation

HRID 1784083 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.[N:19]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.Cl>>[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:26][CH2:25][CH2:24][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:3][C:4](=[O:18])[N:5]1[CH2:14][CH2:13]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 13441-PyrrolidineethanamineHCID 575910932-chloro-9-methoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 112563099-Methoxy-2-(2-pyrrolidin-1-yl-ethylamino)-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 2-pyrrolidin-1-yl-ethylamine as in Example 1 d, followed by treatment with HCl. 1H-NMR (400 MHz, dB-DMSO) δ 7.64 (d, 1H), 7.59 (br, 1H), 7.00-6.92 (2H), 6.18 (s, 1H), 3.92 (t, 2H), 3.82 (s, 3H), 3.46 (m, 2H), 2.91 (t, 2H), 2.90-2.50 (6H) and 1.76 (4H); MS (ESI) (M+H)+ 341.

Sources & evidence

ORD record
ord-1e5338f5ebdd4ad69327ba6377e40e8b
Source dataset
uspto-grants-2009_03
Patent number
US07501512B2

Reaction notes

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