Maleic Acid → GSK-2245035 maleate

HRID 2367968Notes

Reaction equation

HRID 2367968 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33]>C(O)(C)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[NH2:1][C:2]1[N:10]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 44623937Gsk-2245035

Product 1

HCID 53342522GSK-2245035 maleateYield 61.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

6-amino-2-{[(1S)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)pentyl]-7,9-dihydro-8H-purin-8-one (for example, as prepared for Reference Example 1) (0.384 g, 0.98 mmol) was dissolved in isopropyl alcohol (4.6 mL, 12 vols) and heated to 40° C. Maleic acid (0.114 g, 0.98 mmol) was added. A clear solution was obtained. During cooling to room temperature, precipitation occurred. The slurry was filtered, washing with isopropyl alcohol (5 mL) and dried under reduced pressure at 40° C. to constant weight. 6-amino-2-{[(1S)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)pentyl]-7,9-dihydro-8H-purin-8-one, maleate salt (0.305 g, 61% th) was obtained as a white solid.

Workup

  1. customA clear solution was obtained
  2. temperatureDuring cooling to room temperature
  3. customprecipitation
  4. filtrationThe slurry was filtered
  5. washwashing with isopropyl alcohol (5 mL)
  6. customdried under reduced pressure at 40° C. to constant weight

Sources & evidence

ORD record
ord-272fe083014a41e19c4783dd6e94a8a3
Source dataset
uspto-grants-2014_04
Patent number
US08703754B2

Reaction notes

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