Trifluoroacetic acid → HCID 178420884, compound

HRID 2047529Notes

Reaction equation

HRID 2047529 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]2[CH:34]=[CH:33][C:10]3[N:11]=[C:12]([C@@H:14]4[CH2:17][C@H:16]([N:18]5[CH2:25][C@@H:24]6[C@@H:20]([N:21](C(OC(C)(C)C)=O)[CH2:22][CH2:23]6)[CH2:19]5)[CH2:15]4)[S:13][C:9]=3[CH:8]=2)[CH:4]=[N:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCl>[NH:21]1[CH2:22][CH2:23][C@@H:24]2[CH2:25][N:18]([C@@H:16]3[CH2:17][C@H:14]([C:12]4[S:13][C:9]5[CH:8]=[C:7]([C:5]6[CH:4]=[N:3][CH:2]=[N:1][CH:6]=6)[CH:34]=[CH:33][C:10]=5[N:11]=4)[CH2:15]3)[CH2:19][C@H:20]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452023HCID 178452023, compound

Product 1

HCID 178420884HCID 178420884, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by mixing the product of Example 38B with 1:1 mixture of TFA and dichloromethane. After 2 hours, the solvent was removed under reduced pressure, the residue was basified with saturated sodium bicarbonate and extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (0.5% ammonium hydroxide and 5% methanol in dichloromethane) to provide the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 9.19-9.26 (s, 1H) 9.01 (s, 2H) 8.09 (d, J=8.54 Hz, 1H) 8.05 (d, J=1.53 Hz, 1H) 7.65 (dd, J=8.54, 1.83 Hz, 1H) 3.81-3.92 (m, 1H) 3.60-3.71 (m, 1H) 3.03-3.12 (m, 1H) 2.95-3.03 (m, 1H) 2.87-2.95 (m, 1H) 2.72-2.79 (m, 1H) 2.64-2.71 (m, 2H) 2.50-2.62 (m, 3H) 2.32-2.46 (m, 3H) 1.91-2.00 (m, 1H) 1.57-1.67 (m, 1H). MS: (M+H)+=378.

Workup

  1. customThe title compound was prepared
  2. customthe solvent was removed under reduced pressure
  3. extractionextracted three times with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography (0.5% ammonium hydroxide and 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a4edc2949a284d46ae7cc40e33304973
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

Loading…