Hydrazine hydrate (1:1) → HCID 59442813, compound

HRID 243558Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:13]=[C:14]([C:19](=O)[CH:20]=[C:21](SC)SC)[CH:15]=[CH:16][C:17]=1[Cl:18].O.[NH2:28][NH2:29]>C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]([C:19]2[NH:29][N:28]=[C:21]([N:8]3[CH2:9][CH2:10][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6][CH2:7]3)[CH:20]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

Conditions

Temperature: 80 °C

Procedure

1,4-dioxa-8-azaspiro[4.5]decane (2.2 ml) is added to a solution of 1-(3,4-dichlorophenyl)-3,3-bis(methylthio)prop-2-en-1-one (2.0 g) in ethanol (70 ml) and heated to 80° C. over night. Hydrazine-hydrate (1 ml) is added to the reaction mixture and the mixture is stirred over night at 80° C. The solvent is removed under reduced pressure. The crude product is purified using reverse phase HPLC (Varian C18 Microsorb) eluting with a gradient of 10-100% acetonitrile in water containing 0.2% trifluoroacetic acid to give 8-(5-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane (550 mg). m/z(+) 354/356/358 (M+H+).

Workup

customThe solvent is removed under reduced pressure
customThe crude product is purified
washeluting with a gradient of 10-100% acetonitrile in water containing 0.2% trifluoroacetic acid

Sources & evidence

ORD record: ord-d089c545048c45ad85140a9f088f2dbe
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653262B2

Reaction notes

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