1,1'-Carbonyldiimidazole → 1h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-n-[2-[(phenylmethyl)amino]ethyl]-

HRID 2112119Notes

Reaction equation

HRID 2112119 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.[CH2:37]([NH:44][CH2:45][CH2:46]N)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[CH2:37]([NH:44][CH2:45][CH2:46][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])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 77801N-BenzylethylenediamineHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 426111241h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-n-[2-[(phenylmethyl)amino]ethyl]-Yield 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 at for 18 hours, the reaction was treated with N1-benzyl-ethane-1,2-diamine (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 MeOH/CH2Cl2 to provide compound 11g-5 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 MeOH/CH2Cl2
  5. customto provide compound

Sources & evidence

ORD record
ord-0399b0e353a64ec9a46076750a9ea1d6
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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