Propane, 2,2',2''-[methylidynetris(oxy)]tris- → HCID 18187329, compound

HRID 1357650Notes

Reaction equation

HRID 1357650 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:18]=[O:19])([C:14]([F:17])([F:16])[CH3:15])[C:4]=2[CH:3]=1.[CH:22]([O:31][CH:32]([CH3:34])[CH3:33])([O:27][CH:28]([CH3:30])[CH3:29])OC(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.O>C(O)(C)C.C(Cl)Cl>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:22]([O:27][CH:28]([CH3:29])[CH3:30])[O:31][CH:32]([CH3:33])[CH3:34])([C:14]([F:17])([F:16])[CH3:15])[C:4]=2[CH:3]=1.[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:18]=[O:19])([C:14]([F:16])([F:17])[CH3:15])[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 78191Propane, 2,2',2''-[methylidynetris(oxy)]tris-HCID 521998p-Toluenesulfonic acid monohydrateHCID 18187313HCID 18187313, compound

Product 2

HCID 18187313HCID 18187313, compoundHCID 18187329HCID 18187329, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

Method PP: To a stirred solution of 7-chloro-5-formyl-5-(1,1-difluoroethyl)-5,10-dihydrobenzo[b][1,8]naphthyridine (51) (619 mg, 2.005 mmol) in anhydrous triisopropyl orthoformate (30.0 mL, 134 mmol), anhydrous isopropanol (10 mL) and anhydrous methylene chloride (10 mL) at room temperature was added p-TsOH.H2O (763 mg, 4.010 mmol). After 18 h at room temperature, the reaction was quenched with saturated aqueous NaHCO3 (25 mL), and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Flash chromatography (30%-40% EtOAc-hexane, gradient elution) afforded 53 (400 mg, 49% yield) as a yellow solid as well as 45% recovery of starting material 51 (280 mg).

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3 (25 mL)
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash chromatography (30%-40% EtOAc-hexane, gradient elution)

Sources & evidence

ORD record
ord-bf02564507c64935938e666056d77af7
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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