Diisopropylethylamine → HCID 86687162, compound

HRID 1402321Notes

Reaction equation

HRID 1402321 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH2:19]([N:22]([CH2:26][CH:27]=[CH2:28])[C:23](Cl)=[O:24])[CH:20]=[CH2:21]>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:23]([N:22]([CH2:26][CH:27]=[CH2:28])[CH2:19][CH:20]=[CH2:21])=[O:24])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3449313Diallylcarbamyl chlorideHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 86687162HCID 86687162, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-fluoro-pyridin-2-yl)-hydrazine (for reference procedure see WO 2010/022076, which is incorporated herein by reference in its entirety; 2.54 g, 20.0 mmol) in DCM (150 mL) and DIPEA (3.87 g, 30.0 mmol) was added N,N-di-2-propen-1-yl-carbamic chloride (for reference procedure see for example Tetrahedron 1996, 52, 13739-13750, which is incorporated herein by reference in its entirety; 4.13 g, 26.0 mmol) and the reaction mixture was stirred at RT for 18 h. The reaction mixture was diluted with MeOH (50 mL) and loaded onto an SCX cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3 in MeOH. The compound containing fractions were concentrated in vacuo and the resulting residue was purified by FCC on silica, using a gradient of 0-6% [2M NH3 in MeOH] in DCM, to afford the title compound (2.30 g, 46%) as a yellow solid. LCMS (Method 1): Rt 2.26 min, m/z 251 [MH+].

Workup

  1. washThe cartridge was washed with MeOH
  2. washthe product eluted with 2M NH3 in MeOH
  3. additionThe compound containing fractions
  4. concentrationwere concentrated in vacuo
  5. customthe resulting residue was purified by FCC on silica

Sources & evidence

ORD record
ord-8a4df530ac714dd38c302c550e76139e
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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