Tetrahydrofuran → HCID 136954200, compound

HRID 632511Notes

Reaction equation

HRID 632511 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:5][C:4]=1/[CH:17]=[CH:18]/[C:19](=O)[CH2:20][C:21](=O)/[CH:22]=[CH:23]/[C:24]1[NH:25][CH:26]=[CH:27][CH:28]=1.C1COCC1.O.[NH2:37][NH2:38].C([O-])(O)=O.[Na+]>CC(O)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1/[CH:17]=[CH:18]/[C:19]1[CH:20]=[C:21](/[CH:22]=[CH:23]/[C:24]2[NH:25][CH:26]=[CH:27][CH:28]=2)[NH:38][N:37]=1)[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)2×HCID 516892Sodium BicarbonateHCID 117888779HCID 117888779, compound

Product 1

HCID 136954200HCID 136954200, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

To 30 mg of (1E,6E)-1-[2-methoxy-4-(2-pyridylmethoxy)phenyl]-7-(1H-pyrrol-2-yl)hepta-1,6-diene-3,5-dione were added 1 mL of THF, 3 μL of AcOH and 4 μL of hydrazine monohydrate, and the mixture was stirred at 60° C. for 4 hours. To this, 500 μL of AcOH was added and the mixture was stirred at 80° C. for 1 hour. To this, 4 μL of hydrazine monohydrate was added and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was allowed to cool back to room temperature, and a saturated aqueous NaHCO3 solution was added. After extraction with AcOEt, the organic layer was separated. The obtained organic layer was washed with saturated brine, dried over MgSO4, and concentrated. The residue was purified by PTLC (CHCl3/methanol or AcOEt system) to give 8 mg of the title compound (27% yield).

Workup

  1. stirringthe mixture was stirred at 80° C. for 1 hour
  2. stirringthe mixture was stirred at 80° C. for 1 hour
  3. temperatureto cool back to room temperature
  4. extractionAfter extraction with AcOEt
  5. customthe organic layer was separated
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by PTLC (CHCl3/methanol or AcOEt system)

Sources & evidence

ORD record
ord-195fd793d8f74c00b13a975febe1eff0
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Reaction notes

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