Sodium Hydroxide → HCID 67025194, compound

HRID 1512868Notes

Reaction equation

HRID 1512868 reaction equation
[OH-].[Na+:2].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([C:28]([O-:30])=[O:29])=[CH:22]4)[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:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([C:28]([O-:30])=[O:29])=[CH:22]4)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].[Na+:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58222473HCID 58222473, compound

Product 1

HCID 67025194HCID 67025194, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Aqueous NaOH solution (2 N, 2 mL) was added to a solution of 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-2-carboxylate (D23) (65 mg) in ethanol (8 mL) at RT. The resulting solution was heated to 50° C. and stirred at that temperature for 30 min. The reaction mixture was cooled to RT and stirred for 30 min. Ethanol was evaporated. The solid was filtered and washed with water. The solid was collected and dried to afford sodium 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-2-carboxylate (E8) (50 mg) as a white solid. δH (CD3OD, 400 MHz): 1.44 (6H, d), 4.86 (1H, m), 7.08 (1H, d), 7.32 (1H, d), 7.56 (1H, d), 7.94 (1H, dd), 8.15 (1H, dd), 8.24 (1H, d), 8.43 (1H, t). MS (ES): C20H26ClN3O4Na requires 419; found 398.1 (M—Na++2H+).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. stirringstirred for 30 min
  3. customEthanol was evaporated
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customThe solid was collected
  7. customdried

Sources & evidence

ORD record
ord-cdef484b2f2e4f95aff3e741cfecb1c6
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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