Sodium Bicarbonate → HCID 57896719, compound

HRID 2421908Notes

Reaction equation

HRID 2421908 reaction equation
O=[C:2]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:3][NH:4][C:5]([C:7]1[CH:29]=[N:28][C:10]2[O:11][CH2:12][CH2:13][N:14]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:9]=2[CH:8]=1)=O.C([O-])(=O)C.[NH4+:40].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:30]1([C:2]2[NH:40][C:5]([C:7]3[CH:29]=[N:28][C:10]4[O:11][CH2:12][CH2:13][N:14]([S:15]([C:18]5[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:22][CH:23]=5)(=[O:17])=[O:16])[C:9]=4[CH:8]=3)=[N:4][CH:3]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 57896683HCID 57896683, compound

Product 1

HCID 57896719HCID 57896719, compoundYield 860.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-oxo-2-phenylethyl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxamide (40 mg, 0.079 mmol) in DMF (1 mL) was added ammonium acetate (61 mg, 0.791 mmol). The reaction was subjected to microwave irradiation (150° C., 30 min). The reaction mixture was treated with saturated aqueous NaHCO3 (1 mL) and extracted with EtOAc (2×1 mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated. The residue was purified by flash column chromatography using a gradient elution of hexanes with 25-100% EtOAc Providing 7-(5-phenyl-1H-imidazol-2-yl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (33 mg, 0.68 mmol, 86% yield) as a white/brown solid. LCMS (+ESI) m/z=487.0 [M+H]+; 1H-NMR (CDCl3) δ 8.69-8.67 (m, 2H), 7.82 (d, 2H), 7.75 (d, 2H), 7.72 (d, 2H), 7.42 (s, 1H), 7.36 (t, 2H) 7.26 (m, 2H) 3.95 (m, 2H), 3.84 (m, 2H).

Workup

  1. customThe reaction was subjected to microwave irradiation (150° C., 30 min)
  2. extractionextracted with EtOAc (2×1 mL)
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash column chromatography
  7. washa gradient elution of hexanes with 25-100% EtOAc

Sources & evidence

ORD record
ord-0383449ea74d40529bf878f818736460
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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