Sodium hydride → HCID 67980735, compound

HRID 1427458Notes

Reaction equation

HRID 1427458 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[N:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[H-].[Na+].CS(O[CH:25]([C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=1)[CH2:26][CH2:27][CH3:28])(=O)=O>CN(C)C=O.C(OCC)(=O)C>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[N:13][C:12]([NH:15][CH:25]([C:29]3[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=3)[CH2:26][CH2:27][CH3:28])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 49758339HCID 49758339, compoundHCID 86667300HCID 86667300, compound

Product 1

HCID 67980735HCID 67980735, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-(4-(trifluoromethyl)phenyl)pyridazin-3-amine (140 mg, 0.585 mmol) in N,N-dimethylformamide (2 mL) was added to a suspension of 60% sodium hydride (27.2 mg, 0.679 mmol) in N,N-dimethylformamide (2 mL) at 0° C. The mixture was stirred at room temperature for 30 minutes. A mixture of ethyl 4-(1-(methylsulfonyloxy)butyl)benzoate (0.170 g, 0.566 mmol) in N,N-dimethylformamide (3 mL) was then added at room temperature. The reaction was stirred for 2 hours. The reaction was diluted with ethyl acetate and washed with water and brine. The organics were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-15% ethyl acetate in heptanes) gave ethyl 4-(1-(6-(4-(trifluoromethyl)phenyl)pyridazin-3-ylamino)butyl)benzoate (25.0 mg, 10%) as an oil. 1H NMR (400 MHz, CDCl3, δ): 7.98-8.05 (m, 4H), 7.67 (d, J=8.19 Hz, 2H), 7.53 (d, J=9.36 Hz, 1H), 7.44 (d, J=8.19 Hz, 2H), 6.57 (d, J=9.36 Hz, 1H), 5.56-5.67 (m, 1H), 4.82-4.93 (m, 1H), 4.34 (q, J=7.22 Hz, 2H), 1.79-2.01 (m, 2H), 1.36 (t, J=7.22 Hz, 3H), 1.28-1.54 (m, 2H), 0.96 (t, J=7.32 Hz, 3H). MS (M+1): 444.1.

Workup

  1. additionwas then added at room temperature
  2. stirringThe reaction was stirred for 2 hours
  3. washwashed with water and brine
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (0-15% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-4db033579fb241e5b678ae1bc4c21667
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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