Triethylamine → HCID 66707411, compound

HRID 1848352Notes

Reaction equation

HRID 1848352 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([C:12]3([CH2:15][NH2:16])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.Cl[C:25]([O:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:26].C([O-])(O)=O.[Na+]>C1COCC1.O>[CH:28]1([O:27][C:25](=[O:26])[NH:16][CH2:15][C:12]2([C:10]3[N:11]=[C:4]4[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][N:5]4[N:9]=3)[CH2:14][CH2:13]2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2735892Cyclopentyl chloroformateHCID 58074577HCID 58074577, compound

Product 1

HCID 66707411HCID 66707411, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere C-[1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropyl]-methylamine (0.063 g, 0.29 mmol) was dissolved in THF (1 mL) and Et3N (0.06 mL, 0.43 mmol). Cyclopentyl chloroformate (0.053 g, 036 mmol) was added. Stirring was performed at RT for 24 h. Aq. NaHCO3 and H2O were added. The aqueous phase was extracted with DCM (×3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using toluene:EtOAc 2:1->1:1 as the eluent to afford [1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-carbamic acid cyclopentyl ester.

Workup

  1. extractionThe aqueous phase was extracted with DCM (×3)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-7f22cb49e9cb4f3d99d0e7842ba413b7
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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