Benzylamine → HCID 23114545, compound

HRID 748848Notes

Reaction equation

HRID 748848 reaction equation
[C:1](=O)([O:29]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[C:5]([CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])=[N:6][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:8][CH:9]=1.CN1CCOCC1.[CH2:47]([NH2:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.CCCCCC>ClCCl>[CH2:47]([NH:54][C:1](=[O:29])[O:2][CH2:3][C:4]1[C:5]([CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])=[N:6][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 8058HexaneHCID 23114589HCID 23114589, compound

Product 1

HCID 23114545HCID 23114545, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the [6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methylpyridin-3-yl]methyl 4-nitrophenyl carbonate (51 mg, 0.089 mmol) in dichloromethane (1 ml) were successively added N-methylmorpholine (0.020 ml, 0.18 mmol) and benzylamine (0.012 ml, 0.11 mmol) at 0° C. The resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was washed with a saturated aqueous solution of ammonium chloride. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. A fraction obtained from the elution portion with hexane:ethyl acetate=4:1 was concentrated under reduced pressure. The solid thus obtained was washed with diisopropyl ether and collected by filtration, whereby the title compound (33 mg, 0.060 mmol, 68%) was obtained as a white solid.

Workup

  1. customat 0° C
  2. washThe reaction mixture was washed with a saturated aqueous solution of ammonium chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationethyl acetate=4:1 was concentrated under reduced pressure
  8. customThe solid thus obtained
  9. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-8580370a4feb49b69589d2bfdac0b193
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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