Triethylamine → HCID 11663113, compound

HRID 272302Notes

Reaction equation

HRID 272302 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][NH:8][CH2:7][C:6]=2[CH:27]=1.C(N(CC)CC)C.[CH3:35][N:36]([CH3:41])[S:37](Cl)(=[O:39])=[O:38]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][N:8]([S:37]([N:36]([CH3:41])[CH3:35])(=[O:39])=[O:38])[CH2:7][C:6]=2[CH:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chloride2×HCID 11696573HCID 11696573, compound

Product 1

HCID 11663113HCID 11663113, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the compound from example 5 (270 mg, 0.71 mmol) in dichloromethane (20 mL) was added triethylamine (118.8 μL, 0.86 mmol) followed by dimethylsulfamoyl chloride (84 μL, 0.78 mmol) and the reaction mixture was stirred for 16 hours. Dimethylsulfamoyl chloride (84 μL, 0.78 mmol) was then added and the reaction stirred for a further 72 hours. The reaction was diluted with water (20 mL) and the phases separated. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give the crude residue. Purification by column chromatography on silica gel using ethyl acetate and then dichloromethane methanol (95:5) as eluent gave the product as a white crystalline solid, 217 mg (63%).

Workup

  1. stirringthe reaction stirred for a further 72 hours
  2. customthe phases separated
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give the crude residue
  7. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-7294e6c347224daa81100eb20384f873
Source dataset
uspto-grants-2008_11
Patent number
US07456170B2

Reaction notes

Loading…