Hydrochloric Acid → HCID 178461883, compound

HRID 928540Notes

Reaction equation

HRID 928540 reaction equation
[Cl: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][CH:14]=1)[C:8]([C@@H:19]([NH:21][C:22]1[N:30]=[CH:29][N:28]=[C:27]3[C:23]=1[N:24]=[CH:25][N:26]3C1CCCCO1)[CH3:20])=[CH:7]2.Cl>C(O)C>[N:30]1[C:22]([NH:21][C@H:19]([C:8]2[N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10](=[O:12])[C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[CH3:20])=[C:23]2[C:27]([NH:26][CH:25]=[N:24]2)=[N:28][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666077098-Chloro-2-phenyl-3-[(1S)-1-[[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]amino]ethyl]-1(2H)-isoquinolinone

Product 1

HCID 178461883HCID 178461883, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (Compound 9) and 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (Compound 4) are combined in the presence of triethylamine and isopropyl alcohol. The reaction solution is heated at 82° C. for 24 hours to afford Compound 10. The intermediate compound 10 is treated with concentrated HCl and ethanol under aqueous conditions at 35° C. to remove the tetrahydropyranyl group to yield (S)-3-(1-(9H-purin-6-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one. Isolation/purification under aqueous conditions affords polymorph Form C.

Workup

  1. customto remove the tetrahydropyranyl group

Sources & evidence

ORD record
ord-ebc6b86a3c754b16a350478664cdea26
Source dataset
uspto-grants-2016_03
Patent number
US09290497B2

Reaction notes

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