Diethylamine → HCID 67107644, compound

HRID 2177850Notes

Reaction equation

HRID 2177850 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[C:6]([O:10][C:11]([N:13]1[CH2:16][CH2:15][CH:14]1[C:17]([OH:19])=O)=[O:12])([CH3:9])([CH3:8])[CH3:7].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([N:3]([CH2:4][CH3:5])[C:17]([CH:14]1[CH2:15][CH2:16][N:13]1[C:11]([O:10][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:12])=[O:19])[CH3:2]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 36238861-[(Tert-butoxy)carbonyl]azetidine-2-carboxylic acid2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67107644HCID 67107644, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of diethylamine (0.453 g), azetidine-1,2-dicarboxylic acid-1-t-butyl ester (Intermediate 209, 0.891 g), HATU (2.53 g) and DIPEA (1.72 g) in acetonitrile (20 ml) was stirred at room temperature under argon for 4 hours. The mixture was evaporated to dryness and ethyl acetate was added to the residue. The solution was washed with 1M NaOH, brine and water then dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-4% to give t-butyl 2-diethylcarbamoylazetidine-1-carboxylate (0.733 g) as light brown oil.

Workup

  1. customThe mixture was evaporated to dryness and ethyl acetate
  2. additionwas added to the residue
  3. washThe solution was washed with 1M NaOH, brine and water
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of methanol and DCM with a gradient of 0-4%

Sources & evidence

ORD record
ord-25d2f1df4aea4b0d9e0d888e96e96f74
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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