Triphenylphosphine → HCID 68765039, compound

HRID 2391599Notes

Reaction equation

HRID 2391599 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([N:7]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[N:9]=[CH:8]2)[S:4][C:3]=1[C:16]([O:18]C)=O.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C@@H:27](O)[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:49](C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C@H:27]([O:1][C:2]1[CH:6]=[C:5]([N:7]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[N:9]=[CH:8]2)[S:4][C:3]=1[C:16]([NH2:49])=[O:18])[CH3:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6999091(1S)-1-(2-chlorophenyl)ethan-1-olHCID 68765327methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

Product 1

HCID 68765039HCID 68765039, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere 100 mg of methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate, 57.2 mg of (1S)-1-(2-chlorophenyl)ethanol and 95.7 mg triphenylphosphine are dissolved in 1 ml anhydrous THF. To this mixture a solution of 80.9 mg diisopropyl azodicarboxylate in 0.5 ml anhydrous THF is added dropwise and the mixture is stirred for 14 h at room temperature. The solvent is evaporated under vacuum. After extraction with ethyl acetate and a saturated solution of sodium chloride, the organic phase is dried over MgSO4. The solvent is removed under vacuum and the remaining residue is dissolved in 2 ml dichloromethane and filtered through a short plug of silica gel (eluent: ethyl acetate). After evaporation of the solvent, the remaining residue and 20 ml of a saturated solution of ammonia in methanol are stirred in a microwave vial at 125° C. for 8 h in the microwave cavity. Subsequently the solvent is removed under vacuum. The remaining residue is dissolved in 2 ml dichloromethane and is purified by flash chromatography (eluent: ethyl acetate, followed by ethyl acetate/methanol 95/5 (v/v)) to yield the title compound.

Workup

  1. customThe solvent is evaporated under vacuum
  2. extractionAfter extraction with ethyl acetate
  3. dry with materiala saturated solution of sodium chloride, the organic phase is dried over MgSO4
  4. customThe solvent is removed under vacuum
  5. dissolutionthe remaining residue is dissolved in 2 ml dichloromethane
  6. filtrationfiltered through a short plug of silica gel (eluent: ethyl acetate)
  7. customAfter evaporation of the solvent
  8. stirringthe remaining residue and 20 ml of a saturated solution of ammonia in methanol are stirred in a microwave vial at 125° C. for 8 h in the microwave cavity
  9. customSubsequently the solvent is removed under vacuum
  10. dissolutionThe remaining residue is dissolved in 2 ml dichloromethane
  11. customis purified by flash chromatography (eluent: ethyl acetate, followed by ethyl acetate/methanol 95/5 (v/v))

Sources & evidence

ORD record
ord-ff57a3bbb00b4fe5a4f4378d906f7b6a
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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