Trichloroacetyl isocyanate → HCID 59026695, compound

HRID 606078Notes

Reaction equation

HRID 606078 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:21]=2)[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:18]=1)[CH3:2].ClC(Cl)(Cl)C([N:36]=C=O)=O>ClCCl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:21]=2)[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:36])[C:8]=2[N:18]=1)[CH3:2]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 67041399HCID 67041399, compound

Product 1

HCID 59026695HCID 59026695, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridine (1.64 g, 3.90 mmol) in anhydrous dichloromethane (50 mL) was cooled to 6° C., and a solution of trichloroacetyl isocyanate (0.51 mL, 4.29 mmol) in dichloromethane (5 mL) was added dropwise. The solution was stirred for 30 minutes, and then the solvent was removed under reduced pressure. The residue was treated with sodium methoxide in methanol (10 mL of a 25% w/w solution) and methanol (40 mL). The resulting mixture was stirred for 18 hours at room temperature. A precipitate was present and was isolated by filtration, washed with methanol and diethyl ether, and dried under high vacuum at 80° C. for 18 hours to provide 0.999 g of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a white solid, mp 190.0-191.0° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was treated with sodium methoxide in methanol (10 mL of a 25% w/w solution) and methanol (40 mL)
  3. stirringThe resulting mixture was stirred for 18 hours at room temperature
  4. customwas isolated by filtration
  5. washwashed with methanol and diethyl ether
  6. customdried under high vacuum at 80° C. for 18 hours

Sources & evidence

ORD record
ord-15976821148240bfb0fd347b6239f62f
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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