Hydrazine hydrate (1:1) → HCID 90449662, compound

HRID 1411261Notes

Reaction equation

HRID 1411261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:19](=[O:40])[NH:20][C:21]3[S:22][C:23]([S:26][CH2:27][CH2:28][N:29]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:24][N:25]=3)[C:5]2=[CH:6][CH:7]=1.O.NN>C(O)C>[NH2:29][CH2:28][CH2:27][S:26][C:23]1[S:22][C:21]([NH:20][C:19]([N:8]2[C:5]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9]2)=[O:40])=[N:25][CH:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90449804HCID 90449804, compound

Product 1

HCID 90449662HCID 90449662, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 5-chloro-1-((5-((2-(1,3-dioxoisoindolin-2-yl)ethyl)thio)thiazol-2-yl)carbamoyl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (56 mg, 0.094 mmol) was dissolved in ethanol (3 mL). Thereafter, hydrazine monohydrate (0.007 mL, 0.14 mmol) was added to the above obtained solution, and the thus obtained mixture was then stirred at 90° C. for 3 hours. Thereafter, insoluble matters were removed by filtration, and the reaction solution was then concentrated in vacuo. The obtained residue was purified by preparative thin-layer column chromatography (chloroform:saturated ammonium methanol=10:1) to obtain the captioned compound (20 mg, 46%) in the form of a white solid.

Workup

  1. customThereafter, insoluble matters were removed by filtration
  2. concentrationthe reaction solution was then concentrated in vacuo
  3. customThe obtained residue was purified by preparative thin-layer column chromatography (chloroform:saturated ammonium methanol=10:1)

Sources & evidence

ORD record
ord-67447d7430f444e5ba31a39a4becf2e8
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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