Hydrazine hydrate (1:1) → HCID 90449639, compound

HRID 1411321Notes

Reaction equation

[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[N:10]([C:18]([NH:20][C:21]3[S:22][C:23]([S:26][CH2:27][CH2:28][CH2:29][N:30]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:24][N:25]=3)=[O:19])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].O.NN>C(O)C>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[N:10]([C:18]([NH:20][C:21]3[S:22][C:23]([S:26][CH2:27][CH2:28][CH2:29][NH2:30])=[CH:24][N:25]=3)=[O:19])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

1′-Acetyl-5-chloro-N-(5-((3-(1,3-dioxoisoindolin-2-yl)propyl)thio)thiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (0.93 g, 1.57 mmol) was dissolved in ethanol (30 mL). Thereafter, a hydrazine hydrate (0.12 g, 2.36 mmol) was added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred at 90° C. for 3.5 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (chloroform:methanol=4:1) to obtain the captioned compound (0.56 g, 77%) in the form of a colorless solid.

Workup

concentrationThereafter, the reaction solution was concentrated in vacuo
customthe obtained residue was then purified by silica gel column chromatography (chloroform:methanol=4:1)

Sources & evidence

ORD record: ord-b9c98a74489a480aa0c554f9da05ec0d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921576B2

Reaction notes

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