Benzenesulfonic Acid → 5-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one benzenesulfonate

HRID 393906Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([C:15]2[NH:16][C:17](=[O:32])[C:18]3[C:19](=[C:21]([CH2:30][CH3:31])[N:22]([CH:24]4[CH2:27][N:26]([CH2:28][CH3:29])[CH2:25]4)[N:23]=3)[N:20]=2)[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[C:33]1([S:39]([OH:42])(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OCC)(=O)C>[C:33]1([S:39]([OH:42])(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:1]([C:4]1[CH:5]=[C:6]([C:15]2[NH:16][C:17](=[O:32])[C:18]3[C:19](=[C:21]([CH2:30][CH3:31])[N:22]([CH:24]4[CH2:27][N:26]([CH2:28][CH3:29])[CH2:25]4)[N:23]=3)[N:20]=2)[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

5-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (88 mg, 0.2 mmol) was dissolved in warm ethyl acetate (2 mL). A solution of benzenesulfonic acid (32 mg, 0.2 mmol) in ethyl acetate (2 ml) was then added, giving a precipitate. This mixture was warmed to 50° C. for 15 minutes, then allowed to cool to 0° C. The resulting solid was filtered, washed with ethyl acetate and dried in vacuo, to afford the title compound as a white solid 89 mg (74%).

Workup

customgiving a precipitate
temperatureto cool to 0° C
filtrationThe resulting solid was filtered
washwashed with ethyl acetate
customdried in vacuo

Sources & evidence

ORD record: ord-687399ae7d49421ab99a133dc87b24eb
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809200B2

Reaction notes

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