1,1'-Carbonyldiimidazole → HCID 67412620, compound

HRID 2112127Notes

Reaction equation

HRID 2112127 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.[C:37]([O:41][C:42]([N:44]1[CH2:48][CH2:47][CH:46](N)[CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38]>C1COCC1>[C:37]([O:41][C:42]([N:44]1[CH2:48][CH2:47][CH:46]([NH:18][C:16]([C:15]2[CH:14]=[C:13]3[C:9]([CH:10]=[N:11][N:12]3[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:8][C:7]=2[O:6][C:5]2[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=2)=[O:17])[CH2:45]1)=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27563701-Boc-3-aminopyrrolidineHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 67412620HCID 67412620, compoundYield 94%

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 3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (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-13 as an oil in 94% 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-13 as an oil in 94% yield

Sources & evidence

ORD record
ord-5c9710739a754c258d32ef912b7970ac
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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