Triethylamine → HCID 71293437, compound

HRID 2362322Notes

Reaction equation

HRID 2362322 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:34])[N:20]([CH2:22][CH2:23][CH2:24][N:25](C(OC(C)(C)C)=O)[CH3:26])[N:21]=[C:8]2[N:7]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=2)[C:6]=1[CH3:45])=[O:4].C(N(CC)CC)C.[CH3:53][S:54](Cl)(=[O:56])=[O:55]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:34])[N:20]([CH2:22][CH2:23][CH2:24][N:25]([S:54]([CH3:53])(=[O:56])=[O:55])[CH3:26])[N:21]=[C:8]2[N:7]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=2)[C:6]=1[CH3:45])=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71293456HCID 71293456, compound

Product 1

HCID 71293437HCID 71293437, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of Intermediate 18 (0.12 g, 0.19 mmol) in DCM (2.5 mL) and TFA (0.25 mL) was added. The resulting mixture was stirred at RT for 1 hour and then evaporated in vacuo. The resulting residue was taken up in DCM (4 mL), and then triethylamine (105 μL, 0.75 mmol) added, followed by methanesulfonyl chloride (28 μL, 0.36 mmol). The reaction mixture was stirred at RT for 30 mins and then partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM as eluent to yield the title compound as a white solid (106 mg).

Workup

  1. customevaporated in vacuo
  2. stirringThe reaction mixture was stirred at RT for 30 mins
  3. custompartitioned between EtOAc and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer further extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with a gradient of 0-10% MeOH in DCM as eluent

Sources & evidence

ORD record
ord-943924a125de440e942af586f35c9f29
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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