HCID 57991631, compound → HCID 57991638, compound

HRID 556039Notes

Reaction equation

HRID 556039 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:10][C:9]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:10][C:9]=1[C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 57991631HCID 57991631, compound

Product 1

HCID 57991638HCID 57991638, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a 100 ml three-necked flask were added 0.60 g (1.43 mmol) N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-4-fluoro-benzamide prepared in Example 4 and 15 ml dichloromethane, maintaining the temperature at lower than −10° C. in ice salt bath, and then added dropwise 1.7 ml of 1.763 mol/L BBR3 solution in dichloromethane. Upon the completion of addition, the resulting mixture was stirred at that temperature for 1 hour and then at room temperature for 1 hour, added 2 g ice, distilled under a reduced pressure to remove dichloromethane, and then added 20 ml ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under a reduced pressure to give a crude product, which was recrystallized with ethyl acetate/petroleum ether to obtain a 0.39 product as a white solid in a yield of 67.2%, mp: 205-206 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.22 (2H, s, CH2), 6.84 (2H, d, J=8.68 Hz, ArH), 7.23˜7.39 (7H, m, ArH), 7.47 (2H, d, J=8.68 Hz, ArH), 8.15 (2H, dd, 3JHH=9.00, 4JFH=5.64 Hz, ArH), 9.62 (1H, s, OH), 12.66 (1H, s, CONH); EI-MS m/e (%): 404.1 (M+, 100), 123.0 (70); HREI-MS Calcd. for C23H17FN2O2S: 404.0995. found: 404.0988.

Workup

  1. additionUpon the completion of addition
  2. waitat room temperature for 1 hour
  3. distillationdistilled under a reduced pressure
  4. customto remove dichloromethane
  5. additionadded 20 ml ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under a reduced pressure
  11. customto give a crude product, which
  12. customwas recrystallized with ethyl acetate/petroleum ether
  13. customto obtain a 0.39 product as a white solid in a yield of 67.2%, mp

Sources & evidence

ORD record
ord-558a68138356465a84a46091d6e95afb
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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