Water → 5-[2-Ethoxy-5-(4-ethylpiperazine-1-sulfonyl)pyridin-3-yl]-3-ethyl-2-(2-methoxyethyl)-2,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 348411Notes

Reaction equation

HRID 348411 reaction equation
C(OC(=O)C)C.[CH2:7]([O:9][C:10]1[N:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][C:11]=1[C:27]1[NH:28][C:29](=[O:42])[C:30]2[C:31](=[C:33]([CH2:40][CH3:41])[N:34]([CH2:36][CH2:37][O:38][CH3:39])[N:35]=2)[N:32]=1)[CH3:8].O>C(O)C>[CH2:7]([O:9][C:10]1[N:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]2)(=[O:17])=[O:18])=[CH:12][C:11]=1[C:27]1[NH:28][C:29](=[O:42])[C:30]2[C:31](=[C:33]([CH2:40][CH3:41])[N:34]([CH2:36][CH2:37][O:38][CH3:39])[N:35]=2)[N:32]=1)[CH3:8]

Participants

4

Reactant 2

HCID 962WaterHCID 135790108HCID 135790108, compound

Product 1

HCID 1355369435-[2-Ethoxy-5-(4-ethylpiperazine-1-sulfonyl)pyridin-3-yl]-3-ethyl-2-(2-methoxyethyl)-2,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (0.019 mol) of the compound of Example 8 and Example 102, 1-{6-ethoxy-5-[3-ethyl-6,7-dihydro-2-(2-methoxyethyl)-7-oxo-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-pyridylsulfonyl}-4-ethylpiperazine ethyl acetate solvate, was charged followed by 12 ml/g (120 mls) of 16% water in ethyl alcohol. The slurry was heated to reflux to yield a solution and 6 ml/g (60 mls) distilled off at atmospheric pressure. The solution was then cooled to room temperature with crystallisation occurring at 40° C. The slurry was then cooled to 5–10° C. and granulated for 30 minutes following which it was filtered and washed with 2 ml/g ethyl alcohol (20 mls). The damp solid was dried in vacuo overnight at 55–60° C. to yield a white crystalline solid. (Yield 7.6 g, 76%). Melting Point 162–165° C.

Workup

  1. temperatureThe slurry was heated
  2. temperatureto reflux
  3. customto yield a solution and 6 ml/g (60 mls)
  4. distillationdistilled off at atmospheric pressure
  5. customoccurring at 40° C
  6. temperatureThe slurry was then cooled to 5–10° C.
  7. filtrationwas filtered
  8. washwashed with 2 ml/g ethyl alcohol (20 mls)
  9. customThe damp solid was dried in vacuo overnight at 55–60° C.
  10. customto yield a white crystalline solid

Sources & evidence

ORD record
ord-b86dc8f36241433291795230d90cfdee
Source dataset
uspto-grants-2007_02
Patent number
US07176311B2

Reaction notes

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