Triethylamine → HCID 66598076, compound

HRID 1189225Notes

Reaction equation

HRID 1189225 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]1[N:7]([CH2:15][CH2:16][C:17]#[C:18][C:19]2[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=2)[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12.CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([N:25]([C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([C:18]#[C:17][CH2:16][CH2:15][N:7]2[N:8]=[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]3=[N:6]2)[N:24]=1)[S:2]([CH3:1])(=[O:4])=[O:3])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66598045HCID 66598045, compound

Product 1

HCID 66598076HCID 66598076, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (98 mg, 0.85 mmol) in DCM was added to a solution of 6-(4-benzotriazol-2-yl-but-1-ynyl)-pyridin-2-ylamine (100 mg, 0.38 mmol, Example 169(A)) and Et3N (0.12 mL, 0.85 mmol) in DCM (2 mL). The reaction mixture was stirred at room temperature for 2 hours and then the solvent was evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2) to yield 140 mg (0.33 mmol, 88%) of N-methylsulfonyl-N-[6-(4-benzo[d][1,2,3]triazol-2-yl-but-1-ynyl)-pyridin-2-yl]-methylsulfonamide as a white solid.

Workup

  1. customthe solvent was evaporated
  2. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2)

Sources & evidence

ORD record
ord-57bd883c219b4b5292db64ddd6320d87
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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