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

HRID 909129Notes

Reaction equation

HRID 909129 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-225e60cdb1a641b094ff59e2c902ced5
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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