Tetrahydrofuran → HCID 59743401, compound

HRID 1947010Notes

Reaction equation

HRID 1947010 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[CH:11]=[N:10]2)[CH:6]=[CH:5][N:4]=1.C1C[O:22][CH2:21][CH2:20]1>C(Cl)(=O)C.C(N(CC)CC)C.C(Cl)Cl.CO>[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:21](=[O:22])[CH3:20])[CH:16]=3)[CH:11]=[N:10]2)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 2

HCID 8028TetrahydrofuranHCID 59743355HCID 59743355, compound

Product 1

HCID 59743401HCID 59743401, compound

Reagents, catalysts & solvents 4

HCID 6367Acetyl chlorideCatalystHCID 8471TriethylamineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (10 drops) was added dropwise at RT to 1-(2-methylsulfanylpyrimidin-4-yl)-1H-indazol-6-ylamine (0.13 g, 0.5 mmol) and triethylamine (15 drops) in THF (5 mL), and the resulting mixture stirred for 30 min. The reaction mixture was diluted with DCM and MeOH, washed twice with aqueous NaHCO3 and once with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was treated with Et2O and hexane, and the precipitate was collected by filtration to give N-[1-(2-methylsulfanylpyrimidin-4-yl)-1H-indazol-6-yl]-acetamide (146 mg) as an off-white solid.

Workup

  1. washwashed twice with aqueous NaHCO3 and once with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionThe crude residue was treated with Et2O and hexane
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-031537616a1d43c3b56b1c735b6567e3
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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