Sodium Hydroxide → HCID 44193857, compound

HRID 2076081Notes

Reaction equation

HRID 2076081 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][C:18]3[CH2:24][CH2:23][CH2:22][CH:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]=3[N:20]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[OH-].[Na+]>ClC(Cl)C>[CH3:14][C:12]1[N:11]=[CH:10][N:9]([C:8]2[CH:7]=[CH:6][C:5]([NH:15][C:16]3[S:17][C:18]4[CH2:24][CH2:23][CH2:22][CH:21]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:19]=4[N:20]=3)=[CH:4][C:3]=2[OH:2])[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 42647277N-[3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-4-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine

Product 1

HCID 44193857HCID 44193857, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine (200 mg, 0.48 mmol) in dichloroethane (4.8 mL) was added under nitrogen at room temperature borontribromide (528 uL, 0.53 mmol) and the reaction was refluxed for 2 hours. The same amount of borontribromide was added and the reaction was refluxed for 2 hours, again the same amount of borontribromide was added and the reaction was refluxed for 1 hour, stirred at room temperature for 3 days. The reaction was set to pH 7 with aqueous sodium hydroxide and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel using dichloromethane/methanol/concentrated aqueous ammonia (9:1:0.1 v/v/v) as eluent to yield the title compound (70 mg, 36%) as a beige solid. MS ISP (m/e): 403.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.06 (s, 2H), 7.64 (s, 1H), 7.25-7.31 (m, 2H), 7.17 (t, 1H), 7.00-7.11 (m, 6H), 4.04 (m, 1H), 2.71 (m, 2H), 2.19 (m, 1H), 2.13 (s, 3H), 1.66-1.85 (m, 3H).

Workup

  1. additionwas added under nitrogen at room temperature borontribromide (528 uL, 0.53 mmol)
  2. temperaturethe reaction was refluxed for 2 hours
  3. additionThe same amount of borontribromide was added
  4. temperaturethe reaction was refluxed for 2 hours
  5. additionagain the same amount of borontribromide was added
  6. temperaturethe reaction was refluxed for 1 hour
  7. extractionextracted three times with ethyl acetate
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-bc7b708b546c41df9ae8416ceebb9899
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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