1,1'-Carbonyldiimidazole → HCID 67411822, compound

HRID 909135Notes

Reaction equation

HRID 909135 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](N)=[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][NH:38][CH:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1>C1COCC1>[CH3:37][N:38]([CH:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1)[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:4]=[CH:3][C:2]([F:1])=[CH:24][CH:23]=1)=[O:17]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5663231-Methyl-4-(methylamino)piperidineHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 67411822HCID 67411822, compoundYield 3%

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 methyl-(1-methyl-piperidin-4-yl)-amine (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-11 as an oil in 3% 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-11 as an oil in 3% yield

Sources & evidence

ORD record
ord-401251c44a824f0da044241f2de224dd
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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