Water → HCID 178490667, compound

HRID 1037942Notes

Reaction equation

HRID 1037942 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[OH2:24]>CN(C)C=O>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:6][CH2:5][C:1]([OH:24])([CH3:3])[CH3:2])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

Product 1

HCID 178490667HCID 178490667, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 244A (75 mg, 0.23 mmol) in N,N-dimethylformamide (2 mL) was treated with NaH 60% dispersion in oil (9.5 mg, 0.23 mmol) followed by Example 308A (60 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 18 hours, poured into water and extracted with ethyl acetate. The organic layer was washed with H2O (2×50 mL), dried over MgSO4, filtered, concentrated under reduced pressure and dried under vacuum (˜1 mm Hg) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.17 (s, 6H), 1.32 (s, 9H), 1.76-1.91 (m, 2H), 3.79 (s, 3H), 4.14-4.31 (m, 2H), 4.43 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 7.31 (s, 1H), 7.44 (dd, J=9.0, 2.9 Hz, 1H), 7.76 (d, J=3.1 Hz, 1H); MS (ESI) m/z 411 (M+H)+. Anal. Calculated for C20H27ClN2O3S C, 58.45; H, 6.62; N, 6.82. Found C, 58.30; H, 6.51; N, 6.71.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with H2O (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customdried under vacuum (˜1 mm Hg)

Sources & evidence

ORD record
ord-cefb1a1b798c444f9e84375766cba262
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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