Dimethylcarbamoyl Chloride → 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-yl dimethylcarbamate

HRID 1003337Notes

Reaction equation

HRID 1003337 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:14]3[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34].CO.C(Cl)Cl>ClCCCl>[CH3:31][N:32]([CH3:36])[C:33](=[O:34])[O:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:11][O:12][C:13]=2[CH:18]=1

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21226129Dichloromethane methanolHCID 1358150593-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol

Product 1

HCID 187964373-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-yl dimethylcarbamateYield 26.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol (Example 9) (1.5 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.13 g) in 1,2-dichloroethane (40 ml) was added dimethylcarbamyl chloride (0.65 g). The mixture was refluxed for 24 hours under N2. TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered and the filtrate concentrated in vacuo. Flash chromatography (silica gel) eluting with 5% acetone/5% MeOH/CH2Cl2 provided a residue which upon crystallization afforded 0.5 g of the product, m.p. 150° C.

Workup

  1. temperatureThe mixture was refluxed for 24 hours under N2
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. washFlash chromatography (silica gel) eluting with 5% acetone/5% MeOH/CH2Cl2
  5. customprovided a residue which
  6. customupon crystallization

Sources & evidence

ORD record
ord-70542ba70ee84ff4934e9abe082c7937
Source dataset
uspto-grants-2000_04
Patent number
US06046203

Reaction notes

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