Sodium Methoxide → HCID 178457236, compound

HRID 25637Notes

Reaction equation

HRID 25637 reaction equation
[CH3:1][N:2]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]#[C:23][CH2:24][N:25]([CH3:29])[CH2:26][CH2:27][CH3:28])[CH2:18][CH2:17]1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[CH:8][CH:7]=1)(=[O:5])=[O:4].C[O-].[Na+]>CO>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([S:3]([N:2]([CH3:1])[C@H:16]2[CH2:17][CH2:18][C@H:19]([C:22]#[C:23][CH2:24][N:25]([CH3:29])[CH2:26][CH2:27][CH3:28])[CH2:20][CH2:21]2)(=[O:5])=[O:4])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178457237HCID 178457237, compound

Product 1

HCID 178457236HCID 178457236, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 44.3 mg (0.1 mmol) of trans-N-[4-(Methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-sulfamoyl)-phenyl]-acetamide in 5 ml MeOH was treated with 0.37 ml (2 mmol) of sodium methylate (5.4 M in MeOH) and heated at 70° C. for 30 h. The solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 97:3) gave 31 mg (82%) of pure trans-4-Amino-N-methyl-N-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-benzenesulfonamide, MS: 378 (MH+).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-7c04a66f3d4a467797cf326bb790148e
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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