Trifluoromethanesulfonic anhydride → HCID 88921461, compound

HRID 1470491Notes

Reaction equation

HRID 1470491 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[O:30](S(C(F)(F)F)(=O)=O)[S:31]([C:34]([F:37])([F:36])[F:35])(=O)=[O:32]>C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[S:31]([O:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([C:13]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[O:14])=[CH:4][CH:3]=1)(=[O:32])=[O:30]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 68281903HCID 68281903, compound

Product 1

HCID 88921461HCID 88921461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-hydroxy-8-methylnaphthalen-1-yl)(morpholino)methanone (above Step-7 intermediate) (1 equiv) in dry CH2Cl2 (4 mL) under nitrogen was added DIPEA (3 equiv) at 0° C. and the mixture was stirred for 10 min. To this, Tf2O (1.5 equiv) was added drop wise and the reaction mixture was stirred for another 1.5 h at 0° C. Then it was slowly quenched with water (10 mL) and the aqueous layer was extracted with CH2Cl2 (4×10 mL). The combined organic layer was washed with water (10 mL), brine (10 mL), dried (Na2SO4) and filtered. The solvent was removed under reduced pressure and the residue was purified by column to give the title compound.

Workup

  1. stirringthe reaction mixture was stirred for another 1.5 h at 0° C
  2. customThen it was slowly quenched with water (10 mL)
  3. extractionthe aqueous layer was extracted with CH2Cl2 (4×10 mL)
  4. washThe combined organic layer was washed with water (10 mL), brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column

Sources & evidence

ORD record
ord-2ad5e0a0726f4bb08585e34925e7fe98
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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