Hydrazine hydrate (1:1) → HCID 66835993, compound

HRID 2404450Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of {3-[(benzothiazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}acetic acid methyl ester (30 mg) in absolute ethanol (1 mL) is added hydrazine hydrate (0.1 mL). The reaction mixture is heated at 80° C. for 18 hours. Solvent and volatiles are removed under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol from 95/5 to 80/20) to give {3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}acetic acid hydrazide.

Workup

customSolvent and volatiles are removed under reduced pressure
customThe residue is purified by chromatography (gradient dichloromethane/methanol from 95/5 to 80/20)

Sources & evidence

ORD record: ord-52912a5d3b7b419cb52276c5b334e8c6
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802664B2

Reaction notes

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