Triethylamine → HCID 67517550, compound

HRID 2038790Notes

Reaction equation

HRID 2038790 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][N:13]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(O[N:29]1[N:37]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.O.NN>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:29][NH2:37])=[O:17])=[CH:14][N:13]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67508334HCID 67508334, compound

Product 1

HCID 67517550HCID 67517550, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(1-tert-butoxycarbonylamino-cyclopropyl)-nicotinic acid (0.50 g, 1.8 mmol) in DMF (3 mL) was added HATU (0.68 g, 1.8 mmol), Et3N (0.25 mL, 1.8 mmol) and the mixture allowed to stir at room temperature for 20 min. Hydrazine monohydrate (0.09 mL, 1.8 mmol) was then added and the reaction stirred for 1 h. The mixture was diluted with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, brine and dried with MgSO4. The mixture was filtered and concentrated to give [1-(5-hydrazinocarbonyl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.51 g, 1.7 mmol) as a yellow solid, m/z 293.7 [M+H]+.

Workup

  1. stirringthe reaction stirred for 1 h
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03d9ce01f06f4f7c9411580d0a953f85
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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