Sodium Hydroxide → HCID 25062824, compound

HRID 2189814Notes

Reaction equation

HRID 2189814 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][N:21]4[CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[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:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][N:21]4[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[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 59316740HCID 59316740, compound

Product 1

HCID 25062824HCID 25062824, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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) (1.5 g, 3.20 mmol) in hot ethanol (15 ml) was treated with sodium hydroxide (7.5 ml, 15.00 mmol) and stood for 1 hr. The solvents were evaporated and the residue partitioned between ethyl acetate/water. Acetic acid was added to adjust the pH to 5 and the layers separated. The organic layer was dried over magnesium sulphate and evaporated. The crude material was triturated with ether to give the title compound (1.1 g) as a white solid. 5H (d6-DMSO, 400 MHz): 1.37 (6H, d), 2.08 (2H, m), 2.23 (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. customThe solvents were evaporated
  2. customthe residue partitioned between ethyl acetate/water
  3. additionAcetic acid was added
  4. customthe layers separated
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. customevaporated
  7. customThe crude material was triturated with ether

Sources & evidence

ORD record
ord-0f2b3c720ec24d2eb187011149d77e23
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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