Triethylamine → HCID 21262789, compound

HRID 567952Notes

Reaction equation

HRID 567952 reaction equation
[F:1][CH:2]([F:36])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].CCN(CC)CC.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[F:36][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([NH:35][S:45]([CH3:44])(=[O:47])=[O:46])=[CH:33][CH:34]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21262826HCID 21262826, compound

Product 1

HCID 21262789HCID 21262789, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of amine from Step 1 above (200 mg, 0.4 mmol) in 6 mL of CH2Cl2 was added 0.28 mL (2.0 mmol) of Et3N followed by 0.11 mL (1.4 mmol) of methylsulfonyl chloride. The solution was stirred at 0° C. for 1.5 h, quenched with water and diluted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in 10 mL of a 1:1:1 mixture of THF:MeOH: 1 N K2CO3, stirred for 3.5 h at room temperature, quenched with a saturated aqueous NH4Cl solution and diluted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (100% ethyl acetate) to afford the methyl sulfonamide as a foam (114 mg, 51%).

Workup

  1. customquenched with water
  2. additiondiluted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 10 mL of a 1:1:1 mixture of THF
  7. stirringMeOH: 1 N K2CO3, stirred for 3.5 h at room temperature
  8. customquenched with a saturated aqueous NH4Cl solution
  9. additiondiluted with ethyl acetate
  10. washThe organic layer was washed with brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by flash chromatography on silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-b6db43bf30e040c0bc8a0266962aa86b
Source dataset
uspto-grants-2001_01
Patent number
US06180650B2

Reaction notes

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