Tetrahydrofuran → HCID 57484109, compound

HRID 2112123Notes

Reaction equation

HRID 2112123 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]([N:32]1[CH:36]=[CH:35]N=[CH:33]1)(N1C=CN=C1)=O.[CH2:37]1COCC1>>[CH3:33][N:32]([CH3:25])[CH2:36][CH2:35][CH2:37][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 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 57484109HCID 57484109, compoundYield 44%

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 N-1-dimethyl-propane-1,3-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-9 as an oil in 44% 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

Sources & evidence

ORD record
ord-4c74b1415c524aaf8d6fe3f37434179b
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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