Triethylamine → HCID 68379173, compound

HRID 2038791Notes

Reaction equation

HRID 2038791 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[C:38]([O:42][C:43](=[O:58])[NH:44][C:45]1([C:48]2[CH:53]=[CH:52][C:51]([C:54]([NH:56][NH2:57])=[O:55])=[CH:50][N:49]=2)[CH2:47][CH2:46]1)([CH3:41])([CH3:40])[CH3:39]>CN(C=O)C.O>[C:38]([O:42][C:43](=[O:58])[NH:44][C:45]1([C:48]2[CH:53]=[CH:52][C:51]([C:54]([NH:56][NH:57][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:6])=[O:55])=[CH:50][N:49]=2)[CH2:47][CH2:46]1)([CH3:41])([CH3:39])[CH3:40]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67517550HCID 67517550, compound

Product 1

HCID 68379173HCID 68379173, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of cyclopropyl carboxylic acid (0.20 g, 0.68 mmol) in DMF (2 mL) was added HATU (0.26 g, 0.68 mmol), Et3N (0.10 mL, 0.75 mmol) and the reaction mixture was allowed to stir at room temperature for 20 min. [1-(5-Hydrazinocarbonyl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.20 g, 0.68 mmol) in DMF (1 mL) was added and the reaction allowed to stir at room temperature for 21 h. The mixture was diluted with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with satd NaHCO3, brine and dried with MgSO4. The mixture was filtered and concentrated to give {1-[5-(N′-cyclopropane-carbonyl-hydrazinocarbonyl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester (0.23 g, 0.64 mmol) as a light brown solid, m/z 361.7 [M+H]+.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined extracts were washed with satd NaHCO3, brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-704a4e2506aa4d278296f0af3a04bfd1
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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