Triethylamine → HCID 89862352, compound

HRID 1497018Notes

Reaction equation

HRID 1497018 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2(O)[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:18][CH2:17][C:12]3([O:13][CH2:14][CH2:15][O:16]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 65916912HCID 65916912, compound

Product 1

HCID 89862352HCID 89862352, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Intermediate 3A (1.87 g, 6.19 mmol) and Et3N (1.724 mL, 12.37 mmol) in DCM (30 mL) was added a solution of methanesulfonyl chloride (0.53 mL, 6.8 mmol) in DCM (10 mL) over 1 h at rt. The reaction mixture was stirred at rt for 2.5 h. Additional Et3N (1.724 mL, 12.37 mmol) and methanesulfonyl chloride (0.53 mL, 6.8 mmol) were added and stirred for another 1 h. The reaction mixture was partitioned between 1 N HCl and DCM. The organic layer was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure to give Intermediate 3B (1.7 g, 5.9 mmol, 97% yield). LC-MS (ESI) m/z 285 (M+H), RT=3.43 min (Method C).

Workup

  1. stirringstirred for another 1 h
  2. customThe reaction mixture was partitioned between 1 N HCl and DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-577c20b990f64f279ed7d0af1cd48868
Source dataset
uspto-grants-2015_12
Patent number
US09199946B2

Reaction notes

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