Hydrochloric Acid → HCID 44547325, compound

HRID 1512961Notes

Reaction equation

HRID 1512961 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]=[C:24]4[C:20]([C:21]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][NH:23]4)=[CH:19][C:18]=3[F:33])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>C(O)(C)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][NH:23]4)=[CH:19][C:18]=3[F:33])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146137HCID 59146137, compound

Product 1

HCID 44547325HCID 44547325, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl 3-[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoate (D158) (250 mg) in isopropanol (20 mL) and water (4 mL) was added 0.8 mL of 20% NaOH aqueous solution. The mixture was then stirred overnight. Afterwards, the solution was adjusted to pH 3 by addition of concentrated HCl and evaporated in vacuo. The residue was treated with 8 mL DMF. The insolubles were filtered and the filtrate was purified by MDAP. The solvent was freeze dried to give 3-[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoic acid (E111) (80 mg). δH (DMSO-d6, 400 MHz): 1.32 (6H, d), 2.54 (2H, t), 2.88 (2H, t), 5.40 (1H, m), 7.37 (1H, s), 7.48 (1H, d), 8.05 (1H, d), 8.50 (1H, d), 8.87 (1H, d), 11.24 (1H, s), 12.05 (1H, s); δF (DMSO-d6, 376 MHz): −121.6; MS (ES): C21H18ClFN4O4 requires 444; found 445.2 (M+H+).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was treated with 8 mL DMF
  3. filtrationThe insolubles were filtered
  4. customthe filtrate was purified by MDAP
  5. customdried

Sources & evidence

ORD record
ord-7a15c9bb86d94f9593ae944bd017a565
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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