1,1'-Carbonyldiimidazole → HCID 57484110, compound

HRID 2112124Notes

Reaction equation

HRID 2112124 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:25](N1C=CN=C1)([N:27]1[CH:31]=[CH:30]N=[CH:28]1)=O>C1COCC1>[CH3:25][N:27]([CH3:28])[CH2:31][CH2:30][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

4

Reactant 2

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

Product 1

HCID 57484110HCID 57484110, compoundYield 58%

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-dimethyl-ethane-1,2-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-10 as an oil in 58% 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-10 as an oil in 58% yield

Sources & evidence

ORD record
ord-11e2dfeed1e4494caf614fc8b8c04c14
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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