Hydrochloric Acid → HCID 17906310, compound

HRID 852190Notes

Reaction equation

HRID 852190 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]4[CH2:19][O:18]4)=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)C.Cl>CO.C(Cl)(Cl)Cl>[CH2:22]([NH:29][CH2:19][CH:17]([OH:18])[CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:6]2[C:5]3[CH:20]=[CH:21][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)=[CH:14][CH:13]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7504BenzylamineHCID 58928269(R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole

Product 1

HCID 17906310HCID 17906310, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Combine (R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole (29) (500 mg, 1.75 mmol), benzylamine (755 mg, 7.05 mmol), ethanol (5.0 ml) and heat (˜80° C.) for 18.5 hours. At room temperature the reaction solidified. Dissolve reaction mixture with chloroform and concentrate (in vacuo). Purify the compound by column chromatography (silica) eluting with 10% ethanol in chloroform to obtain a white solid. Dissolve the free base in hot methanol and add ethereal HCl to a pH ˜2-3. Concentrate the reaction mixture (in vacuo) and recrystallize (methanol) the salt and dry (60° C., 1.0 mm Hg) to give the title compound as white solid (233 mg, 46% Yield). mp=251-253° C. Microanalysis (C, H, N) is consistent with the final, desired compound. [α]22D=+9.17, c (MeOH)=0.60.

Workup

  1. customAt room temperature
  2. dissolutionDissolve
  3. concentrationconcentrate (in vacuo)
  4. customPurify the compound by column chromatography (silica)
  5. washeluting with 10% ethanol in chloroform
  6. customto obtain a white solid
  7. concentrationConcentrate the reaction mixture (in vacuo)
  8. customrecrystallize (methanol) the salt
  9. customdry (60° C., 1.0 mm Hg)

Sources & evidence

ORD record
ord-773e5c1ea50b40d29ccc0abc1878d1e1
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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