Hydrazine hydrate (1:1) → HCID 58088349, compound

HRID 250289Notes

Reaction equation

HRID 250289 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][C:34]([F:37])([F:36])[F:35])=[N:21][O:22][C:23]=3[CH:24]([CH3:26])[CH3:25])=[CH:13][C:12]=2[CH3:38])=[C:8]([CH3:10])[CH:9]=1)=O.O.[NH2:40][NH2:41]>CCO>[CH:24]([C:23]1[O:22][N:21]=[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][C:34]([F:37])([F:36])[F:35])[C:19]=1[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:7]2[S:6][C:5]([C:3]([NH:40][NH2:41])=[O:2])=[CH:9][C:8]=2[CH3:10])=[C:12]([CH3:38])[CH:13]=1)([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67272482HCID 67272482, compound

Product 1

HCID 58088349HCID 58088349, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-{4-[5-isopropyl-3-(2-trifluoromethoxy-phenyl)-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-4-methyl-thiophene-2-carboxylic acid methyl ester (980 mg, 1.8 mmol) in EtOH (7 mL) is added hydrazine hydrate (5 mL) and the mixture is stirred at 80° C. overnight. The reaction mixture is concentrated under reduced pressure. The residue is partitioned between EtOAc and water. The layers are separated and the organic phase is concentrated under reduced pressure to give 5-{4-[5-isopropyl-3-(2-trifluoromethoxy-phenyl)-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-4-methyl-thiophene-2-carboxylic acid hydrazide (890 mg, 90%) as a light yellow foam. LC-ES/MS m/e 546 (M+1), 100%.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe residue is partitioned between EtOAc and water
  3. customThe layers are separated
  4. concentrationthe organic phase is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c7d00fbb2394ec5a1d7f158df1c7055
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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