Acetic Acid → HCID 18447172, compound

HRID 1269831Notes

Reaction equation

HRID 1269831 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[C:17]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]2)=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][NH:13]2.[C:25](O)(=[O:27])[CH3:26].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(OCC)(=O)C.C1(C)C=CC=CC=1.CN(C)C=O>[C:25]([N:21]1[CH2:22][CH2:23][CH2:24][CH:19]([O:18][C:17]2[C:9]([CH3:8])=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)[CH2:20]1)(=[O:27])[CH3:26]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22934024HCID 22934024, compound

Product 1

HCID 18447172HCID 18447172, compoundYield 76.8%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.14 ml, 1.0 mmol) was added to a mixture of the 4-methyl-5-(piperidin-3-yloxy)-1H-indazole (92 mg, 0.40 mmol) obtained in Example 422, acetic acid (24 mg, 0.40 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (77 mg, 0.40 mmol), 1-hydroxybenzo-triazole (54 mg, 0.40 mmol) and N,N-dimethylformamide (1.5 ml), and the resulting mixture was stirred at room temperature for 19 hours. The mixture was diluted with a mixed solution of ethyl acetate (10 ml)/toluene (10 ml) and washed with water and then a saturated aqueous sodium hydrogencarbonate solution. The mixture washed was dried over potassium carbonate and then concentrated to dryness to obtain 5-[(1-acetylpiperidin-3-yl)oxy]-4-methyl-1H-indazole (84 mg, 76%).

Workup

  1. washwashed with water
  2. washThe mixture washed
  3. dry with materialwas dried over potassium carbonate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-44704d39dc5c4ba9981d5dadce7b8eb1
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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