Methyl iodide → Ammonia

HRID 2308534Notes

Reaction equation

HRID 2308534 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[S:12][C:11]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:10][C:9]=2[C:8]([O:24][CH3:25])=[CH:7][CH:6]=1)(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.IC.CO[CH:52](OC)[CH2:53][NH2:54]>C1COCC1.CC(C)=O>[NH3:4].[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([NH:14][C:11]2[S:12][C:13]3[C:5]([N:4]4[CH:52]=[CH:53][N:54]=[C:1]4[CH3:2])=[CH:6][CH:7]=[C:8]([O:24][CH3:25])[C:9]=3[N:10]=2)=[O:23])=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 87949Lawesson's reagentHCID 89728Aminoacetaldehyde dimethyl acetalHCID 22283414HCID 22283414, compound

Product 2

HCID 222AmmoniaHCID 22283138HCID 22283138, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(7-Acetylamino-4-methoxy-benzothiazol-2-yl)-4-fluoro-benzamide (100 mg, 0.28 mmol) and Lawessons reagent (135 mg, 0.33 mmol) were dissolved in THF (10 ml) and stirred at ambient temperature for 18 h. Removal of the solvent and flash chromatoigraphy (silica, eluent CH2Cl2/2N aqu. NH3 in MeOH 99:1 to 19:1) afforded a yellow solid which was dissolved in acetone (10 ml) and treated with iodomethane (19.8 mg, 1.4 mmol). After 3 h at ambient temperature the solvent was removed and after dissolution in ethanol (10 ml), aminoacetaldehyde dimethyl acetal (15 mg, 1.4 mmol) were added and the mixture stirred for 18 h at room temperature. The solvent was removed and the residue refluxed for 24 h in ethanol (10 ml) and conc. sulfuric acid (1 ml). The mixture was diluted with water (50 ml) and the pH adjusted to 8 with sodium carbonate. It was extracted three times with dichloromethane. The combined organic extracts were dryed with sodium sulfate and the solvebt removed. Flash chromatography (silica, eluent CH2Cl2/2N aqu. NH3 in MeOH 96:4 to 9:1) afforded the title compound as brown solid, MS: m/e=383 (M+H+).

Workup

  1. customRemoval of the solvent and flash chromatoigraphy (silica, eluent CH2Cl2/2N aqu. NH3 in MeOH 99:1 to 19:1)
  2. customafforded a yellow solid which
  3. customAfter 3 h at ambient temperature the solvent was removed
  4. dissolutionafter dissolution in ethanol (10 ml)
  5. stirringthe mixture stirred for 18 h at room temperature
  6. customThe solvent was removed
  7. temperaturethe residue refluxed for 24 h in ethanol (10 ml)
  8. additionThe mixture was diluted with water (50 ml)
  9. extractionIt was extracted three times with dichloromethane
  10. customthe solvebt removed

Sources & evidence

ORD record
ord-3c051baceaf0439db191be6227aad390
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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