(S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide → (S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1426961Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[C@@H:21]([C:22]4[C:23]([O:29]C)=[N:24][CH:25]=[C:26]([F:28])[CH:27]=4)[CH2:20][O:19][C:18]3=[O:31])=[N:13][C:12]=12)=[O:7]>Cl.O1CCOCC1>[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[C@@H:21]([C:22]4[C:23](=[O:29])[NH:24][CH:25]=[C:26]([F:28])[CH:27]=4)[CH2:20][O:19][C:18]3=[O:31])=[N:13][C:12]=12)=[O:7]

Participants

Conditions

Temperature: 85 °C

Procedure

A suspension of (S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (37 mg, 0.08 mmol) in 4N HCl/dioxane (4 mL) was stirred at 85° C. for 17 hours and then at ambient temperature for 48 hours. The resulting solution was concentrated to ½ volume, transferred to a sealed tube, treated with 4N HCl/dioxane (2 mL) and stirred at 100° C. for 2 hours. The heterogeneous mixture was concentrated, dried under reduced pressure and used directly in the next step, assuming 100% yield. MS (apci) m/z=435.1 (M+H).

Workup

waitat ambient temperature for 48 hours
concentrationThe resulting solution was concentrated
customtransferred to a sealed tube
additiontreated with 4N HCl/dioxane (2 mL)
stirringstirred at 100° C. for 2 hours
concentrationThe heterogeneous mixture was concentrated
customdried under reduced pressure

Sources & evidence

ORD record: ord-49ae3800a56f44349c51c00f52588a36
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933084B2

Reaction notes

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