Trifluoroacetic acid → HCID 70800861, compound

HRID 1190842Notes

Reaction equation

HRID 1190842 reaction equation
[C:1]1([C:7]2[CH:34]=[CH:33][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][NH:21][S:22]([NH:25]C(=O)OC(C)(C)C)(=[O:24])=[O:23])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[CH:34]=[CH:33][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][NH:21][S:22](=[O:23])(=[O:24])[NH2:25])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70800909HCID 70800909, compound

Product 1

HCID 70800861HCID 70800861, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 46a (1.16 g, 2.3 mmol) in DCM (10 mL) was added TFA (5 mL) and the reaction mixture stirred for 0.5 h. The reaction mixture was concentrated under reduced pressure then evaporated under reduced pressure from toluene (2×). The residue was diluted with 1.5 M K3PO4 then extracted with DCM (3×). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by silica gel chromatography eluting with 1 to 15% MeOH/DCM to give Compound 46b (68 mg, 74% yield) as a pale brown solid. LCMS=1.71 min using analytical method (B), 402.0 (M+H). 1H NMR (400 MHz, CD3OD) δ 8.24 (d, J=1.5 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.79 (dd, J=8.5, 1.8 Hz, 1H), 7.73-7.65 (m, 2H), 7.47 (t, J=7.7 Hz, 2H), 7.41-7.32 (m, 1H), 4.47 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthen evaporated under reduced pressure from toluene (2×)
  3. additionThe residue was diluted with 1.5 M K3PO4
  4. extractionthen extracted with DCM (3×)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 1 to 15% MeOH/DCM

Sources & evidence

ORD record
ord-e23041182821443c99f3642a51dbb677
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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