Diisopropylethylamine → HCID 86636678, compound

HRID 2075403Notes

Reaction equation

HRID 2075403 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH:47]([C:49](=[O:72])[CH2:50][CH2:51][C@@H:52]([NH:64][C:65](=[O:71])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68])[CH2:53][C:54]1[CH:55]=[N:56][C:57]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:59]=1)[NH2:48]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:5]([NH:48][NH:47][C:49](=[O:72])[CH2:50][CH2:51][C@@H:52]([NH:64][C:65](=[O:71])[O:66][C:67]([CH3:68])([CH3:69])[CH3:70])[CH2:53][C:54]2[CH:55]=[N:56][C:57]([C:60]([F:61])([F:62])[F:63])=[CH:58][CH:59]=2)=[O:7])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 2306533-Fluoro-4-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57991899HCID 57991899, compound

Product 1

HCID 86636678HCID 86636678, compoundYield 262.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3-fluoro-4-nitrobenzoic acid (130 mg, 701 μmol) (commercially available from 3B Scientific Corporation Product List (Order Number 3B3-068221)), HATU (267 mg, 701 μmol), and N,N-diisopropylethylamine (132 μL, 760 μmol) in DMF (4 mL) was stirred at room temperature for 1 hour. This mixture was added dropwise to a mixture of tert-butyl ((1R)-4-hydrazino-4-oxo-1-((6-(trifluoromethyl)-3-pyridinyl)methyl)butyl)carbamate (220 mg, 585 μmol), prepared as shown in Scheme 24, and N,N-diisopropylethylamine (132 μL, 760 μmol) in DMF (3 mL) and the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the remaining residue partitioned between saturated aqueous NaHCO3 (20 mL) and DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting colorless solid was dissolved in MeOH/DCM, absorbed onto silica gel and purified by flash chromatography (silica gel, 2% to 8% MeOH/DCM) to provide tert-butyl ((1R)-4-(2-((3-fluoro-4-nitrophenyl)carbonyl)hydrazino)-4-oxo-1-((6-(trifluoromethyl)-3-pyridinyl)methyl)butyl)carbamate (834 mg, 77%) as a light yellow solid. LCMS (API-ES) m/z: 566.0 (M+Na+).

Workup

  1. customprepared
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. customthe remaining residue partitioned between saturated aqueous NaHCO3 (20 mL) and DCM (20 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with DCM (3×20 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe resulting colorless solid was dissolved in MeOH/DCM
  10. customabsorbed onto silica gel
  11. custompurified by flash chromatography (silica gel, 2% to 8% MeOH/DCM)

Sources & evidence

ORD record
ord-808a0a2e787a42a081c67914e1be81d3
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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