Triethylamine → HCID 66707623, compound

HRID 1848355Notes

Reaction equation

HRID 1848355 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.[N:24]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1.C([O-])(O)=O.[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([C:12]3([CH2:15][NH:16][C:29]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:30])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 709371-Pyrrolidinecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 58074577HCID 58074577, compound

Product 1

HCID 66707623HCID 66707623, 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 (0.050 g, 0.23 mmol) was dissolved in THF (1 mL) and Et3N (0.048 mL, 0.35 mmol). 1-Pyrrolidinecarbonyl chloride (0.032 mL, 0.29 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 to afford Pyrrolidine-1-carboxylic acid [1-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-amide as a crude product.

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

Sources & evidence

ORD record
ord-6a15601722424c26860b62a72fd3d871
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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