Sodium Methoxide → HCID 178449989, compound

HRID 2036851Notes

Reaction equation

HRID 2036851 reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[C:12]([C:14]([NH:16][C:17]2[C:18]([C:29](=[O:31])[NH2:30])=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)=O)[N:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO>[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[C:12]([C:14]2[N:30]=[C:29]([OH:31])[C:18]3[C:17](=[CH:22][CH:21]=[CH:20][C:19]=3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:16]=2)[N:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 670559462-(N-tert-butylsulfamoyl)-N-(2-carbamoylbiphenyl-3-yl)thiazole-4-carboxamide

Product 1

HCID 178449989HCID 178449989, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution 2-(N-tert-butylsulfamoyl)-N-(2-carbamoylbiphenyl-3-yl)thiazole-4-carboxamide (0.11 g, 0.24 mmol) in methanol (10 mL) was added NaOMe (0.25 ml, 25% in MeOH, 1.2 mmol). The resulting mixture was stirred at RT for 16 h. After this time, the reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (40% EtOAc in hexane) to provide (N-tert-butyl-4-(4-hydroxy-5-phenylquinazolin-2-yl)thiazole-2-sulfonamide (0.10 g, 100% yield) as a white solid. LCMS Method V: retention time 2.01 min; [M+1]=441.2.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (40% EtOAc in hexane)

Sources & evidence

ORD record
ord-d4ae3f3dedd54a27af51cac951ed2489
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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