Ethanethiol → HCID 135983746, compound

HRID 902018Notes

Reaction equation

HRID 902018 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:13]3[C:14]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=4)=[N:15][N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(S)C.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:28][C:24]1[N:23]=[C:22]([C:14]2[C:13]([C:7]3[C:6]4[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=4)[N:10]=[CH:9][CH:8]=3)=[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]3[N:15]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 69221227HCID 69221227, compound

Product 1

HCID 135983746HCID 135983746, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-methoxy-4-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (1.3 g, 3.57 mmol) in DMF (36 mL), add ethanethiol (5.3 mL, 71.4 mmol), followed by sodium hydride (60% dispersion in mineral oil, 2.9 g, 71.4 mmol). After all of the gas has evolved, the mixture is heated at 80° C. for 4 hours, then cooled to room temperature. Saturated aqueous NH4Cl (5 mL) is added, and the mixture concentrated. The residue is dissolved in methylene chloride, washed with water and concentrated to give the title compound 1.16 g (93%) as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. concentrationthe mixture concentrated
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washwashed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d475750ba8cc4b40a27a1076e27d2a5d
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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