Trifluoroacetic acid → HCID 59000790, compound

HRID 1594023Notes

Reaction equation

HRID 1594023 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([C:13]1[C:14]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:15]([CH2:38][CH2:39][CH3:40])[N:16]2[C:21]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][C:18]([N:28]1[CH2:37][CH2:36][C:31]3(OCC[O:32]3)[CH2:30][CH2:29]1)=[N:17]2)=[O:12])[CH3:9].C([O-])(O)=O.[Na+]>C1COCC1.O>[CH2:8]([O:10][C:11]([C:13]1[C:14]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:15]([CH2:38][CH2:39][CH3:40])[N:16]2[C:21]=1[C:20]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:19][C:18]([N:28]1[CH2:29][CH2:30][C:31](=[O:32])[CH2:36][CH2:37]1)=[N:17]2)=[O:12])[CH3:9]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59000762HCID 59000762, compound

Product 1

HCID 59000790HCID 59000790, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoroacetic acid (2.5 mL) was added to a solution of 2-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-phenyl-7-propyl-pyrrolo[1,2-b]pyridazine-5,6-dicarboxylic acid diethyl ester (99) (245 mg, 0.47 mmol) in THF (10 mL) and water (1 mL). The reaction mixture was heated to 50° C. for 4 h, poured into aqueous NaHCO3 solution. The mixture was extracted with EtOAc and the organic layer was washed with saturated aqueous NaHCO3, brine, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, 35% EtOAc/hexane) provided the title compound. 1H NMR (DMSO-d6) δ 1.05-1.11 (m, 6H), 1.38 (t, 2H, J=7.0 Hz), 1.83-1.89 (m, 2H), 2.63-2.67 (m, 4H), 3.34 (t, 2H, J=7.8 Hz), 3.71 (q, 2H, J=7.2 Hz), 4.08-4.11 (m, 4H), 4.35 (q, 2H, J=7.2 Hz), 7.05 (s, 1H), 7.60-7.66 (m, 5H). Mass Spectrum (ES+) m/e=478.2 (M+1).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organic layer was washed with saturated aqueous NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica gel, 35% EtOAc/hexane)

Sources & evidence

ORD record
ord-bae91f3841044e04a3b924afcec41aaf
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

Loading…