Morpholine → HCID 21894711, compound

HRID 720783Notes

Reaction equation

HRID 720783 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.N1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>C1COCC1>[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:18]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[O:17])[N:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:11]=[CH:10]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 21894711HCID 21894711, compoundYield 93%

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 morpholine (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-2 as an oil in 93% 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 11g-2 as an oil in 93% yield

Sources & evidence

ORD record
ord-8b575f5469b44f27bcfbaf81d44b0f3a
Source dataset
uspto-grants-2006_11
Patent number
US07135575B2

Reaction notes

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