N-(2-Aminoethyl)piperidine → HCID 57484106, compound

HRID 720787Notes

Reaction equation

HRID 720787 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[C:16]([NH2:18])=[O:17])[N:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:11]=[CH:10]3)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:37]1([CH2:43][CH2:44]N)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>C1COCC1>[N:37]1([CH2:43][CH2:44][NH:18][C:16]([C:15]2[CH:14]=[C:13]3[C:9]([CH:10]=[N:11][N:12]3[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:8][C:7]=2[O:6][C:5]2[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=2)=[O:17])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 33944N-(2-Aminoethyl)piperidineHCID 682631,1'-CarbonyldiimidazoleHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 57484106HCID 57484106, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (compound 10g, prepared as described in Example 46) in THF was treated with carbonyldiimidazole (1.2 equivalents) at room temperature under nitrogen atmosphere. After stirring for 18 hours, the reaction was treated with 2-piperidin-1-yl-ethylamine (1 equivalent). After an additional 18 hours, the solvent was allowed to slowly evaporate and the residue was purified in a Sep Pak cartridge eluting with a gradient of 100% CH2Cl2 to 5% MeOH/CH2Cl2 to provide compound 11g-6 as an oil in 100% yield.

Workup

  1. waitAfter an additional 18 hours
  2. customto slowly evaporate
  3. customthe residue was purified in a Sep Pak cartridge
  4. washeluting with a gradient of 100% CH2Cl2 to 5% MeOH/CH2Cl2
  5. customto provide compound

Sources & evidence

ORD record
ord-f2841c34870f4165ac785f6603ec65fc
Source dataset
uspto-grants-2006_11
Patent number
US07135575B2

Reaction notes

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