Hydrochloric Acid → HCID 86281900, compound

HRID 1052973Notes

Reaction equation

HRID 1052973 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][C:6]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]3[C:16]([CH3:21])=[N:17][O:18][C:19]=3[CH3:20])[CH:13]=2)[NH:8][C:7]1=[O:22])C.O[Li].O.Cl>C1COCC1.CO.O>[CH3:21][C:16]1[C:15]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:22])[C:6]3([CH2:5][C:4]([OH:29])=[O:3])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([CH3:20])[O:18][N:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86281771HCID 86281771, compound

Product 1

HCID 86281900HCID 86281900, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl-2-(5-(3,5-dimethyl isoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl)acetate (35 mg, 0.089 mmol) dissolved in THF/MeOH (2 mL/2 mL) was added LiOH.H2O (40 mg) in H2O (2 mL). The reaction was stirred at room temperature until complete consumption of the starting material as indicated by TLC. The reaction was added water, acidified with 3% HCl until pH<1 and extracted with EtOAc (3×5 mL). The combined extracts were washed with brine, dried over MgSO4 and concentrated under vacuum. The title compound was purified on Pre-TLC to afford the title compound as a white solid (20 mg, 62%). 1H NMR (400 MHz, DMSO-d6) δH 12.17 (s, 1H), 10.56 (s, 1H), 7.41 (s, 1H), 7.35-7.29 (m, 4H), 7.22-7.24 (m, 2H), 6.96 (d, J=8.0 Hz, 1H), 3.29-3.30 (m, 2H), 2.38 (s, 3H), 2.21 (s, 3H). MS (ESI) m/e [M+1]+ 363.

Workup

  1. extractionextracted with EtOAc (3×5 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe title compound was purified on Pre-TLC

Sources & evidence

ORD record
ord-619a2d4555fb4c55829af709418c1488
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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