Dichloromethane → HCID 10181051, compound

HRID 985162Notes

Reaction equation

HRID 985162 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]([CH2:14][N:15]([CH3:17])[CH3:16])=[C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:24][CH3:25])[CH:10]=2)[C:5]1=[O:26].C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(Cl)Cl>CCOCC>[CH3:16][N:15]([CH2:14][C:13]1[N:4]([CH2:3][CH2:2][NH:1][S:35]([CH3:34])(=[O:37])=[O:36])[C:5](=[O:26])[C:6]2[C:11]([C:12]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[CH:10][C:9]([O:24][CH3:25])=[CH:8][CH:7]=2)[CH3:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22555956HCID 22555956, compound

Product 1

HCID 10181051HCID 10181051, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 116 (50 mg, 0.118 mmol), triethylamine (66 μL, 0.472 mmol), methanesulfonyl chloride (12 μL, 0.153 mmol) and methylene chloride (250 μL) were combined under Ar and stirred at room temperature 24 h. Added methylene chloride and washed the contents of the reaction flask with sat. sodium bicarbonate. Dried the organic layer with sodium sulfate (anh.), filtered then rotary evaporated the filtrate. Trituration of the resulting solid with ether gave 117 as a white solid (35 mg, 0.082 mmol, 69.1%).

Workup

  1. washAdded methylene chloride and washed the contents of the reaction flask with sat. sodium bicarbonate
  2. dry with materialDried the organic layer with sodium sulfate (anh.)
  3. filtrationfiltered
  4. customthen rotary evaporated the filtrate

Sources & evidence

ORD record
ord-c80b46d4587043a69ff20ded7375e31c
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

Loading…