Hydrazine → HCID 53349360, compound

HRID 2357094Notes

Reaction equation

HRID 2357094 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CN(C(O[N:31]1[N:39]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(Cl)Cl.CN(C=O)C.NN>C(OCC)(=O)C>[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH:31][NH2:39])=[O:15])=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 5

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22350042dichloromethane N,N-dimethylformamideHCID 533492554-Octyloxy-3-trifluoromethylbenzoic acid

Product 1

HCID 53349360HCID 53349360, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(Octyloxy)-3-(trifluoromethyl)benzoic acid (D5) (600 mg, 1 equiv) was stirred with HATU (859 mg, 1.2 equiv) and DIEA (1.63 mL, 5 equiv) in CH2Cl2-DMF (10 mL, 4:1, 3 equivalents) followed by addition of hydrazine (282 μL, 3 equiv). The reaction mixture was then diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the title compound (661 mg). MS (ESI): 333.08 (MH+)

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e39af83c99b1470cb556c3072d4998b9
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

Loading…