Methanol → HCID 59143444, compound

HRID 1920730Notes

Reaction equation

HRID 1920730 reaction equation
[CH:1]1([CH2:6][C:7]([N:9]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1)([CH3:18])[CH3:17].CO>C1COCC1>[CH:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:12]2[CH2:13][CH2:14][CH2:15][N:9]([C:7](=[O:8])[CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:10][CH2:11]2)=[S:27])=[CH:21][CH:20]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 1451944-Isopropylphenyl isothiocyanateHCID 16774262HCID 16774262, compound

Product 1

HCID 59143444HCID 59143444, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 1-(2-cyclopentyl-acetyl)-1,4-diazepane (100 mg; 0.475 mmol) and 4-isopropylphenyl isothiocyanate (80 mg; 0.45 mmol) were mixed together at room temperature in 5 mL anhydrous THF. The reaction mixture was left stirring overnight, then 1 mL methanol was added and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography on SiO2 using 0-50% EtOAc in hexanes mixtures as eluent, followed by 1-4% methanol in DCM mixtures. The desired product was isolated as a colorless foam, 180 mg (71% yield). ES+MS: 388 amu (MH+).

Workup

  1. waitThe reaction mixture was left
  2. customthe solvents were evaporated in vacuo
  3. customThe crude mixture was purified by flash column chromatography on SiO2 using 0-50% EtOAc in hexanes mixtures as eluent

Sources & evidence

ORD record
ord-74af6682dca34f1891732289ddbca6db
Source dataset
uspto-grants-2012_05
Patent number
US08173638B2

Reaction notes

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