Maleic Acid → HCID 178441805, compound

HRID 705139Notes

Reaction equation

HRID 705139 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([NH2:25])[C:8]2[NH:13][N:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]>CC(O)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[CH2:1]([C:5]1[N:6]=[C:7]([NH2:25])[C:8]2[NH:13][N:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 178441801HCID 178441801, compound

Product 1

HCID 178441805HCID 178441805, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Butyl-3-(6-(pyrrolidin-1-yl)hexyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (197.3 mg) was treated with maleic acid (133 mg, 2.0 eq) before being slurried in IPA (2.0 mL). The resulting reaction mixture was heated to 70° C. resulting in a homogeneous solution which on aging at 70° C. started to precipitate solid. The resulting slurry was found to set solid at 70° C. therefore an additional IPA (2.0 mL) was added to mobilise the slurry. The resulting reaction mixture was allowed to cool slowly to 20° C. and was aged overnight at 20° C. before being filtered and washed with fresh IPA (2×4 mL) to yield a white solid which was oven dried at 40° C. in vacuo (90 mbar) overnight to afford the title compound (294 mg).

Workup

  1. customThe resulting reaction mixture
  2. customresulting in a homogeneous solution which
  3. customon aging at 70° C.
  4. customto precipitate solid
  5. customat 70° C.
  6. additionan additional IPA (2.0 mL) was added
  7. customThe resulting reaction mixture
  8. temperatureto cool slowly to 20° C.
  9. filtrationbefore being filtered
  10. washwashed with fresh IPA (2×4 mL)
  11. customto yield a white solid which
  12. customdried at 40° C. in vacuo (90 mbar) overnight

Sources & evidence

ORD record
ord-507e2396793c4ef5b1799f2fad80950c
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

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