Benzoyl isothiocyanate → HCID 90112953, compound

HRID 521722Notes

Reaction equation

HRID 521722 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:26][CH:25]3[C:21]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)([NH:22][O:23][CH2:24]3)[CH2:20]2)=[N:17][CH:18]=1>O1CCCC1>[F:12][C:13]1[CH:18]=[N:17][C:16]([N:19]2[CH2:26][CH:25]3[C:21]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)([N:22]([C:10]([NH:9][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[S:11])[O:23][CH2:24]3)[CH2:20]2)=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 90109782HCID 90109782, compound

Product 1

HCID 90112953HCID 90112953, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Benzoyl isothiocyanate (511 μL 3.79 mmol) is added drop wise to a stirred solution of 5-(5-fluoropyrimidin-2-yl)-6a-(3-pyridyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (640 mg, 2.23 mmol) in tetrahydrofuran (20 mL) at 0° C. The resulting mixture is stirred at 0° C. for 1 hour and is warmed to room temperature over 1 hour. The solvent is evaporated under vacuum and the resulting residue is purified by silica gel chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (1.1 g, quantitative). ES/MS (m/e): 451 (M+1).

Workup

  1. temperatureis warmed to room temperature over 1 hour
  2. customThe solvent is evaporated under vacuum
  3. customthe resulting residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-6ca166caa66c4a4ab4ff8b9b36f08aa5
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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