Hydrazine hydrate (1:1) → HCID 68454135, compound

HRID 2358864Notes

Reaction equation

HRID 2358864 reaction equation
[C:1]1([NH:7][C:8]2[C:16]3[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[S:10][C:9]=2C(OCC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:30][NH2:31].[C:32]([O-:35])(O)=O.[Na+]>C(OC(O)C)C>[NH:7]([C:8]1[C:16]2[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[S:10][C:9]=1[C:32]([NH:30][NH2:31])=[O:35])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 9865198Ethyl 3-(phenylamino)-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

Product 1

HCID 68454135HCID 68454135, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of Example 1 (200 mg, 0.5 mmol) in ethoxyethanol (5 mL) was added hydrazine hydrate (1.5 mmol). The reaction mixture was heated to 120° C. for 6 h. Upon cooling the reaction mixture was poured into sat NaHCO3 aq and extracted with DCM (×2). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography (silica, 5% EtOH in DCM) gave the title compound (86 mg, 46%). δH (CDCl3) 8.76 (1H, br s), 8.60 (1H, br s), 7.55-7.7 (3H, m), 7.4-7.5 (2H, m), 7.25-7.35 (3H, m), 6.9-7.0 (2H, m), 6.35 (1H, d, J 10 Hz), 4.3 (2H, br s). LCMS (ES+) RT 2.84 minutes, 377 (M+H)+.

Workup

  1. temperatureUpon cooling the reaction mixture
  2. additionwas poured
  3. extractionextracted with DCM (×2)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica, 5% EtOH in DCM)

Sources & evidence

ORD record
ord-297f06aaec354215ad402a5e7adb2fab
Source dataset
uspto-grants-2010_07
Patent number
US07763729B2

Reaction notes

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