Triethylamine → N-[2-(4-valerylamino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide

HRID 2256369Notes

Reaction equation

HRID 2256369 reaction equation
C(O)(=O)C(O)=O.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](Cl)(=[O:49])[CH2:45][CH2:46][CH2:47][CH3:48]>O1CCCC1>[C:44]([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:49])[CH2:45][CH2:46][CH2:47][CH3:48]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 86751129N-[2-(4-amino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide dioxalate

Product 1

HCID 10835560N-[2-(4-valerylamino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 23, as the free base (0.330 g, 1 mmol) and triethylamine (0.15 mL, 1.05 mmol) were stirred in 10.0 mL tetrahydrofuran and cooled briefly in an ice bath. To the mixture was added dropwise valeryl chloride (0.12 mL, 1 mmol) and the resulting mixture was stirred 18 h at room temperature and filtered, and the filtrate was evaporated to 0.385 g oil. Crystallization from diethyl ether provided 0.176 g colorless crystals. Mp 107°-109° C. Mass spectrum, m+ =413. Anal (C23H35N5O2) theory C, 66.80; H, 8.53; N, 16.93; found C, 66.59; H, 8.66; N, 17.04.

Workup

  1. temperaturecooled briefly in an ice bath
  2. filtrationfiltered
  3. customthe filtrate was evaporated to 0.385 g oil
  4. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-6816039ac3a74ca89e3fa7006810eaeb
Source dataset
uspto-grants-1997_08
Patent number
US05654320

Reaction notes

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