Acetyl chloride → HCID 11661405, compound

HRID 2240183Notes

Reaction equation

HRID 2240183 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]1([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[N:23]([CH:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[N:22]=[CH:21][CH:20]=4)[CH:17]=3)[C:12]([CH2:30][CH3:31])=[N:11]2)[CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:27]1[CH2:28][CH2:29][CH:24]([N:23]2[C:19]([C:16]3[CH:17]=[C:18]4[C:13]([C:12]([CH2:30][CH3:31])=[N:11][N:10]4[CH:5]4[CH2:9][CH2:8][CH2:7][CH2:6]4)=[CH:14][CH:15]=3)=[CH:20][CH:21]=[N:22]2)[CH2:25][CH2:26]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11581341HCID 11581341, compound

Product 1

HCID 11661405HCID 11661405, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (7.8 μL, 0.11 mmol) was slowly added to a mixture of 1-cyclopentyl-3-ethyl-6-(1-piperidin-4-yl-1H-pyrazol-5-yl)-1H-indazole (20 mg, 0.055 mmol), triethylamine (15 μL, 0.11 mmol) in methylene chloride (2 mL), and the reaction was stirred for 16 hours at room temperature. Methylene chloride was added and the organic layer was washed with saturated sodium bicarbonate, water, then brine, dried, filtered and concentrated. The residue was dissolved in ethyl acetate and purified by silica gel column chromatography using 100% ethyl acetate as the eluent to afford 18 mg (81%) of 6-[1-(1-acetylpiperidin-4-yl)-1H-pyrazol-5-yl]-1-cyclopentyl-3-ethyl-1H-indazole. LC/MS (EI) tR 4.29 (Method C), m/z 406.3 (M++1).

Workup

  1. washthe organic layer was washed with saturated sodium bicarbonate, water
  2. dry with materialbrine, dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6c9cf284d94b42fa9f750cb4de6bd3b4
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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