Sodium Hydroxide → HCID 67288943, compound

HRID 1626503Notes

Reaction equation

HRID 1626503 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:34])[NH:20][C:21]3[CH:25]=[CH:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=4)[N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([O:37]CC)=[O:36].[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:34])[NH:20][C:21]3[CH:25]=[CH:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=4)[N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([OH:37])=[O:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67288081HCID 67288081, compound

Product 1

HCID 67288943HCID 67288943, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-chloro-7-(4-(1-(3,4-difluorophenyl)-1H-pyrazol-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.067 g, 0.121 mmol) in 3:1 THF/MeOH (1 ml) was added 1M sodium hydroxide (0.133 ml, 0.133 mmol), and the reaction was allowed to stir for 16 hours. The reaction was concentrated, acidified with dilute HCl, and extracted twice with EtOAc. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated to yield the desired product (0.039 g, 0.0742 mmol, 61.3% yield). MS (apci): m/z=526.1 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6aa34381d2e0445c9a91f498e84a36c0
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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