Hydrazine hydrate (1:1) → HCID 58094955, compound

HRID 2282254Notes

Reaction equation

HRID 2282254 reaction equation
[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21](=O)[CH3:22])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[C:5]2[S:6][CH:7]=[CH:8][N:4]2[N:3]=1.O.[NH2:25]N.COC(OC)[N:30]([CH3:32])C>>[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21]3[NH:25][N:30]=[CH:32][CH:22]=3)=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[C:5]2[S:6][CH:7]=[CH:8][N:4]2[N:3]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 66856293HCID 66856293, compound

Product 1

HCID 58094955HCID 58094955, compoundYield 79%

Conditions

Temperature
90 °C

Procedure

A solution of 1-[2-(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)-4-phenyl-1,3-thiazol-5-yl]ethanone (170 mg, 0.5 mmol) obtained by similar manner with Example 110-8 (ii) in N,N-dimethylformamide dimethylacetal (10 mL) was refluxed at 90° C. for 4 h. The reaction mixture was allowed to cool to rt, and the solvent was evaporated. The residue was suspended in EtOH (5 mL), and then was added hydrazine monohydrate (50 mg, 1.0 mmol). The mixture was stirred at 80° C. for 5 h. The mixture was allowed to cool to rt, and then concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=30/70→100/0) to give the title compound (143 mg, 79%) as a yellow solid.

Workup

  1. temperatureto cool to rt
  2. customthe solvent was evaporated
  3. temperatureto cool to rt
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=30/70→100/0)

Sources & evidence

ORD record
ord-6c872b7acf90446a861b52b4250f8afa
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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