Sodium Bicarbonate → HCID 178424313, compound

HRID 1046756Notes

Reaction equation

HRID 1046756 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[C:8]([CH:20]([NH:22][C:23]1[N:31]=[CH:30][N:29]=[C:28]3[C:24]=1[N:25]=[CH:26][N:27]3C1CCCCO1)[CH3:21])=[CH:7]2.C([O-])(O)=O.[Na+]>>[N:31]1[C:23]([NH:22][CH:20]([C:8]2[N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[C:10](=[O:12])[C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])[CH3:21])=[C:24]2[C:28]([NH:27][CH:26]=[N:25]2)=[N:29][CH:30]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 581581818-methyl-3-(1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-2-o-tolylisoquinolin-1(2H)-one

Product 1

HCID 178424313HCID 178424313, compoundYield 54.1%

Procedure

8-Methyl-3-(1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-2-o-tolylisoquinolin-1(2H)-one 4105 (180 mg, 0.36 mmol) was dissolved in MeOH(HCl) (50 mL) and stirred for 2 h. Aqueous NaHCO3 solution was added to the reaction mixture and the pH value was adjusted to 9. The mixture was then filtered and the filtrate was concentrated in vacuo to afford the desired product, 3-(1-(9H-purin-6-ylamino)ethyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one (4106, compound 191 in Table 4) (80 mg, 54% yield) as a yellow solid.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-31f11a0ce5214ad78830754a1bd06e0c
Source dataset
uspto-grants-2013_10
Patent number
US08569323B2

Reaction notes

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