1,1'-Carbonyldiimidazole → HCID 57484111, compound

HRID 2112126Notes

Reaction equation

HRID 2112126 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.[CH3:37][N:38]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:39][CH2:40][CH2:41]N>C1COCC1>[CH3:37][N:38]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:39][CH2:40][CH2:41][NH:18][C:16]([C:15]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:8][C:7]=1[O:6][C:5]1[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=1)=[O:17]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 577774N-(3-Aminopropyl)-N-methylanilineHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 57484111HCID 57484111, compoundYield 78%

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 N1-Methyl-N1-phenyl-propane-1,3-diamine (1 equivalent). After 18 additional 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-12 as an oil in 78% yield.

Workup

  1. customto slowly evaporate
  2. customthe residue was purified in a Sep Pak cartridge
  3. washeluting with a gradient of 100% CH2Cl2 to 5% MeOH/CH2Cl2
  4. customto provide compound 11g-12 as an oil in 78% yield

Sources & evidence

ORD record
ord-3b1812060e794579956bc4118367df14
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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