Sodium Hydroxide → HCID 25060202, compound

HRID 2189815Notes

Reaction equation

HRID 2189815 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22]([CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[N:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59316759HCID 59316759, compound

Product 1

HCID 25060202HCID 25060202, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 4-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]butanoate (D63) (127 mg, 0.27 mmol) was dissolved in ethanol (5 ml) and then sodium hydroxide (11 mg) was added. The reaction mixture was heated at 100° C. for 1 hour in a microwave reactor and then allowed to cool. The resultant solid was separated by filtration and then washed with acetone. Purification by MDAP, followed by freeze drying of the resultant material afforded the title compound (38.1 mg). MS (ES): C22H2135ClN4O4 requires 440; found (MH+) 441.

Workup

  1. temperatureto cool
  2. customThe resultant solid was separated by filtration
  3. washwashed with acetone
  4. customPurification by MDAP
  5. dry with materialdrying of the resultant material

Sources & evidence

ORD record
ord-e0ed15a9250245c7b1288c719ba81f9d
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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