Triethylamine → HCID 22458189, compound

HRID 2184838Notes

Reaction equation

HRID 2184838 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH:27]1([C:25]([N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][S:41]([CH3:40])(=[O:43])=[O:42])[CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:15][CH2:16]2)=[O:26])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18782313HCID 18782313, compound

Product 1

HCID 22458189HCID 22458189, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.22 g of the compound of example 27 and 0.08 mL of triethylamine (TEA) in 5 mL of CH2Cl2, stirred at r.t. under anhydrous nitrogen atmosphere, was added dropwise a solution of 0.04 mL of methanesulphonyl chloride in 0.5 mL of CH2Cl2. The solution was stirred for 6 h at room temperature, afterwards, it was evaporated to dryness in vacuo and the residue was purified by flash chromatography (CH2Cl2-MeCN 9:1) affording 0.10 g (39%) of the title compound.

Workup

  1. customafterwards, it was evaporated to dryness in vacuo
  2. customthe residue was purified by flash chromatography (CH2Cl2-MeCN 9:1)

Sources & evidence

ORD record
ord-0e210f1a09824859ac7a9b8b40ea9697
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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