Sodium Hydroxide → HCID 25062824, compound

HRID 2189813Notes

Reaction equation

HRID 2189813 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH:21]=[N:22][N:23]4[CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH:21]=[N:22][N:23]4[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59316740HCID 59316740, compound

Product 1

HCID 25062824HCID 25062824, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2M Sodium hydroxide (1 ml, 2 mmol) was added to a solution of ethyl 4-[4-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]butanoate (D60) (N2666-13-A1) (0.062 g, 0.132 mmol) in ethanol (5 ml) and the reaction was heated to 80° C. to effect dissolution then left to cool for 2 hours. Evaporated, dissolved in ethyl acetate/water (25 ml of each) and acidified with acetic acid. Organic dried (magnesium sulphate), evaporated, azeotroped with 15 ml of toluene and triturated with ether. Filtered to give the title compound (42 mg) as a white solid. 5H (d6-DMSO, 400 MHz): 1.37 (6H, d), 2.09 (2H, m), 2.24 (2H, t), 4.54 (2H, t), 4.90 (1H, m), 7.47 (1H, d), 7.62 (1H, dd), 7.97 (1H, d), 8.01 (1H, d), 8.17 (1H, dd), 8.26 (1H, d), 8.56 (1H, s). MS (ES): C22H2135ClN4O4 requires 440; found (MH+) 441.

Workup

  1. dissolutiondissolution
  2. waitthen left
  3. temperatureto cool for 2 hours
  4. customEvaporated
  5. dissolutiondissolved in ethyl acetate/water (25 ml of each) and
  6. dry with materialOrganic dried (magnesium sulphate)
  7. customevaporated
  8. customazeotroped with 15 ml of toluene
  9. customtriturated with ether
  10. filtrationFiltered

Sources & evidence

ORD record
ord-ed5ca5a8ef464e2d9433c25f1006861d
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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