Sodium Hydroxide → HCID 44548410, compound

HRID 1512907Notes

Reaction equation

HRID 1512907 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]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59146115HCID 59146115, compound

Product 1

HCID 44548410HCID 44548410, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl 1-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylate (D74) (280 mg) in tetrahydrofuran (10 mL) and methanol (10 mL) stirred at 20° C. was added a solution of sodium hydroxide (54 mg) in water (10 mL) in one charge. The reaction mixture was stirred at 20° C. for 8 hours. The reaction mixture was concentrated and then H2SO4 (0.1 M) solution was added dropwise until no further white precipitate was formed. The solid was filtered and dried to afford 1-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylic acid (E48) (98 mg). δH (DMSO-d6, 400 MHz): 1.38 (6H, d), 1.61-3.02 (9H, m), 3.95 (2H, s), 4.87-4.93 (1H, m), 7.26 (1H, t), 7.45-7.47 (2H, m), 7.96 (1H, s), 7.96 (1H, s), 8.21 (1H, dd), 8.37 (1H, d), 11.07 (1H, s). MS (ES): C26H27ClN4O4 requires 494; found 495.2 (M+H+).

Workup

  1. additioncharge
  2. concentrationThe reaction mixture was concentrated
  3. additionH2SO4 (0.1 M) solution was added dropwise until no further white precipitate
  4. customwas formed
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-3516e63cda89460a8f629f4e9cefd009
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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