Tetrahydrofuran → HCID 18441893, compound

HRID 458428Notes

Reaction equation

HRID 458428 reaction equation
C1COCC1.C([O:8][C:9]([C:11]1[N:12]=[C:13]([C:16]2[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)[N:19]=[C:18]3[N:39]4[CH2:45][CH2:44][CH2:43][N:40]4[C:41](=[O:42])[C:17]=23)[O:14][CH:15]=1)=[O:10])C.[OH-].[Na+]>CCO>[CH2:25]([O:24][C:22]([C:21]1[C:16]([C:13]2[O:14][CH:15]=[C:11]([C:9]([OH:10])=[O:8])[N:12]=2)=[C:17]2[C:41](=[O:42])[N:40]3[CH2:43][CH2:44][CH2:45][N:39]3[C:18]2=[N:19][C:20]=1[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18442001HCID 18442001, compound

Product 1

HCID 18441893HCID 18441893, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A THF (4 mL) of ethyl 4-[4-(ethoxycarbonyl)-1,3-oxazol-2-yl]-5-oxo-2-{2-[4-(trifluoromethyl)phenyl]ethyl}-8,9-dihydro-5H,7H-pyrazolo[1′2′:1,2]pyrazolo[3,4-b]pyridine-3-carboxylate (0.400 g, 0.717 mmol), 0.717 mL of 1 N NaOH and EtOH (0.717 mL) was stirred for 6 h at ambient temperature and then concentrated. The residue was treated with 1 N HCl until acidic and the organics extracted with EtOAc (2×) and then dried (Na2SO4), filtered and concentrated to a yellowish-orange solid and used in the proceeded step with no further purification: 1H NMR (CDCl3, 400 MHz) δ 8.39 (s, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.29 (d, J=7.9 Hz, 2H), 4.12–4.00 (m, 6H)), 3.18–3.08 (m, 4H), 2.81–2.74 (m, 2H), 1.00 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with 1 N HCl until acidic and the
  3. extractionorganics extracted with EtOAc (2×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellowish-orange solid
  7. customused in the proceeded step with no further purification

Sources & evidence

ORD record
ord-34be493524e344dabc8a9f157ee6bd35
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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