Dimethylcarbamoyl Chloride → HCID 69410576, compound

HRID 1592750Notes

Reaction equation

HRID 1592750 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][C:30]([N:29]([CH3:33])[CH3:28])=[O:31])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride2×HCID 8471Triethylamine2×HCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylate

Product 1

HCID 69410576HCID 69410576, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-Boc-4-(2-aminophenyl)-piperazine (270 mg, 1.0 mmol) and Et3N (400 microliter, 2.89 mmol) in 10 mL of CH2Cl2 was added dimethylcarbamyl chloride (135 microliter, 1.48 mmol). After stirring for about 1 hour, DMAP (10 mg) was added. After stirring for about 3 days, another 800 microliter of Et3N and 270 microliter of dimethylcarbamyl chloride were added. After stirring overnight, the solution was diluted with EtOAc, washed with 1 M HCl (2×), saturated sodium bicarbonate, water and brine, and then dried (Na2SO4), filtered and concentrated. Purification by silica gel chromatography (35 g SiO2, 20 to 50% EtOAc/hexanes, over 30 minutes at 35 mL/min) afforded about 20 mg (0.057 mmol, 6%) of the tide compound as a white solid. LRMS: 349.2 (M+1)

Workup

  1. stirringAfter stirring for about 3 days
  2. stirringAfter stirring overnight
  3. washwashed with 1 M HCl (2×), saturated sodium bicarbonate, water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (35 g SiO2, 20 to 50% EtOAc/hexanes, over 30 minutes at 35 mL/min)

Sources & evidence

ORD record
ord-947f8b5e9be7413f8134535c0658bce0
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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