Pyridine → HCID 71269471, compound

HRID 1429388Notes

Reaction equation

HRID 1429388 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([N:14]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[CH2:18][O:17][CH2:16][C@H:15]2[CH2:26][C:27]([NH2:29])=O)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.O(C(C(F)(F)F)=O)C(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([N:14]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[CH2:18][O:17][CH2:16][C@H:15]2[CH2:26][C:27]#[N:29])(=[O:12])=[O:13])[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 71269295HCID 71269295, compound

Product 1

HCID 71269471HCID 71269471, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 23 (100 mg, 0.24 mmol), pyridine (47 mg, 0.6 mmol) and (CF3CO)2O (76 mg, 0.36 mmol) in DCM (5 mL) was stirred at it for 2 hr. The reaction mixture was quenched with water and extracted with DCM. The organic extracts were dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by Prep-TLC to give the desired compound 24 (34 mg, 36% yield). LCMS (m/z): 394.2 (MH+).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with DCM
  3. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by Prep-TLC

Sources & evidence

ORD record
ord-a864fe5206dc480f9344fedd8e196493
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

Loading…