Sodium Bicarbonate → HCID 86667882, compound

HRID 476130Notes

Reaction equation

HRID 476130 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C@H:6]([NH:9][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:7][CH3:8].C([O-])(O)=O.[Na+].[Cl:20][C:21]1[N:26]=[C:25](Cl)[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][N:22]=1>C1COCC1.CCOC(C)=O.[Cl-].[Na+].O>[Cl:20][C:21]1[N:26]=[C:25]([N:9]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C@@H:6]([C:2]2[O:1][CH:5]=[N:4][N:3]=2)[CH2:7][CH3:8])[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][N:22]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 68089400N-[(1R)-1-(1,3,4-oxadiazol-2-yl)propyl]cyclopentanamine

Product 1

HCID 86667882HCID 86667882, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 131718255Brine ethyl acetateSolvent

Procedure

17 N-[(1R)-1-(1,3,4-oxadiazol-2-yl)propyl]cyclopentanamine (199 mg, 1.019 mmol) in anhydrous THF (3.980 mL) was treated with NaHCO3 (342.4 mg, 4.076 mmol) then 2,4-dichloro-5-nitro-pyrimidine (197.7 mg, 1.019 mmol). The reaction was stirred overnight at ambient temperature. The reaction was further stirred at 45° C. for 10 hours, diluted with EtOAc/Brine and extracted EtOAc (×3). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (30% EtOAc/petrol) to give the sub-tilte compound as a pale yellow oil (107 mg, 30%); 1H NMR (400.0 MHz, CDCl3) d 1.03 (3H, t), 1.45-2.80 (10H, m), 3.55 (1H, m), 4.39 (1H, m), 8.31 (1H, s), 8.60 (1H, s); MS ES (+) 353.1.

Workup

  1. stirringThe reaction was further stirred at 45° C. for 10 hours
  2. extractionextracted EtOAc (×3)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (30% EtOAc/petrol)

Sources & evidence

ORD record
ord-6c40c0bb24384bce9c64f8877f82dc4e
Source dataset
uspto-grants-2014_01
Patent number
US08637666B2

Reaction notes

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