1H-Indazol-6-amine → 2-(1H-Indazol-6-ylamino)-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

HRID 1784066Notes

Reaction equation

HRID 1784066 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.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([NH2:28])[CH:26]=2)[CH:21]=[N:20]1>>[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([NH:28][C:2]3[CH:17]=[C:6]4[C:7]5[C:12]([CH2:13][CH2:14][N:5]4[C:4](=[O:18])[N:3]=3)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=5)[CH:26]=2)[CH:21]=[N:20]1

Participants

3

Reactant 2

HCID 814231H-Indazol-6-amineHCID 575910932-chloro-9-methoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 112105722-(1H-Indazol-6-ylamino)-9-methoxy-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 1H-indazol-6-ylamine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 12.95 (br, 1H), 9.76 (s, 1H), 8.60 (s, 1H), 7.96 (s, 1H), 7.72-7.60 (2H), 7.15-6.95 (3H), 6.42 (s, 1H), 4.01 (t, 2H), 3.85 (s, 3H) and 2.98 (t, 2H); MS (ESI) (M+H)+ 360.

Sources & evidence

ORD record
ord-2634d225563c4a6a92ea2b62881e43a7
Source dataset
uspto-grants-2009_03
Patent number
US07501512B2

Reaction notes

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