Dimethylformamide → HCID 59275558, compound

HRID 1877538Notes

Reaction equation

HRID 1877538 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:23]=[C:22]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])[C:21]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36](=[O:47])[NH:37][C:38]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([CH3:40])[CH3:39])[CH:31]=4)=[CH:20][C:13]=3[C:14]=2[C:15]([O:17]CC)=[O:16])=[CH:6][CH:5]=1.CN(C=O)C>C(O)C.CCOC(C)=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:23]=[C:22]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])[C:21]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36](=[O:47])[NH:37][C:38]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([CH3:40])[CH3:39])[CH:31]=4)=[CH:20][C:13]=3[C:14]=2[C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 14798Sodium Hydroxide2×HCID 59275384HCID 59275384, compound

Product 1

HCID 59275558HCID 59275558, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

NaOH (500 μL, 0.500 mmol, 1M aq.) was added to a stirring solution of ethyl 2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxylate (50 mg, 0.080 mmol) in Ethanol (795 μL) at 60° C. The slurry was allowed to stir overnight. DMF (2 mL) was added along with additional portion of NaOH and the mixture was warmed to 70° C. and allowed to stir overnight. The mixture was diluted with EtOAc and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give the titled compound (49 mg, quant). LC-MS retention time: 2.36 min; m/z (MH+): 601. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. stirringto stir overnight
  2. washwashed with 1M HCl
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a0623bfd503c4227891bce826d933b24
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

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