Phenylacetyl chloride → N-[2-(4-benzylcarbonylamino-1-piperidinyl)-ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide oxalate

HRID 399054Notes

Reaction equation

HRID 399054 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].C(O)(=O)C(O)=O.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][C:23]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH:34]([CH3:36])[CH3:35])[N:26]=2)=[O:24])[CH2:16][CH2:15]1.C(N(CC)CC)C.[C:44]1([CH2:50][C:51](Cl)=[O:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:50]([C:51]([NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][NH:22][C:23]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH:34]([CH3:36])[CH3:35])[N:26]=2)=[O:24])[CH2:18][CH2:19]1)=[O:52])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 86751129N-[2-(4-amino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide dioxalate

Product 1

HCID 18969258N-[2-(4-benzylcarbonylamino-1-piperidinyl)-ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide oxalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 23, as the free base (0.310 g, 0.94 mmol) and triethylamine (0.13 mL, 0.94 mmol) were stirred in 10.0 mL tetrahydrofuran and cooled briefly in an ice bath. To the mixture was added dropwise phenylacetyl chloride (0.12 mL, 0.94 mmol) and the resulting mixture was stirred 18 h at room temperature and filtered, and the filtrate was evaporated to an oil. Crystallization as the oxalate salt from ethyl acetate/methanol provided 0.176 g colorless crystals. Mp 168° C. Mass spectrum, m+ =447. Anal (C28H35N5O6) theory C, 62.56; H, 6.56; N, 13.03; found C, 62.61; H, 6.65; N, 12.83.

Workup

  1. temperaturecooled briefly in an ice bath
  2. filtrationfiltered
  3. customthe filtrate was evaporated to an oil
  4. customCrystallization as the oxalate salt from ethyl acetate/methanol

Sources & evidence

ORD record
ord-c7f0235a479d45358a0af09129f53564
Source dataset
uspto-grants-1998_10
Patent number
US05817676

Reaction notes

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