Dimethyl Sulfate → HCID 9807772, compound

HRID 1370536Notes

Reaction equation

HRID 1370536 reaction equation
[CH3:1][N:2]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH3:30])[CH:24]=2)[CH2:14][CH2:13]1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:4].S(OC)(O[CH3:35])(=O)=O.[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42]>CN(C=O)C.C(O)C>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42].[CH3:1][N:2]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH3:30])[CH:24]=2)[CH2:14][CH2:13]1)[C:3](=[N:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[S:4][CH3:35]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 444972Fumaric AcidHCID 18511648HCID 18511648, compound

Product 1

HCID 9807772HCID 9807772, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1 g (2.35 mmol) of the preceding thiourea (10.2) in 10 ml of DMF is treated at 25° C. with 245 μl of dimethyl sulfate, stirred overnight at 25° C. and then heated for 1 h at 60° C. The mixture is evaporated to dryness and the residue is recovered in the usual way and purified by flash chromatography to give 325 mg (Yd: 32%) of a light yellow oil. This oil is taken up in ethanol and salified with a solution of 80 mg of fumaric acid in the same solvent to give 340 mg (Yd: 26%) of compound of formula:

Workup

  1. temperatureheated for 1 h at 60° C
  2. customThe mixture is evaporated to dryness
  3. customthe residue is recovered in the usual way
  4. custompurified by flash chromatography
  5. customto give 325 mg (Yd: 32%) of a light yellow oil
  6. customto give 340 mg (Yd: 26%) of compound of formula

Sources & evidence

ORD record
ord-2acb2266e66b49459f187569aeac18c6
Source dataset
uspto-grants-2003_06
Patent number
US06583159B1

Reaction notes

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