Hydrochloric Acid → HCID 66620348, compound

HRID 538552Notes

Reaction equation

HRID 538552 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([F:32])=[C:6]([CH:28]=[CH:29][C:30]=1[F:31])[O:7][CH2:8][C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)OC(C)(C)C)=[CH:16][CH:15]=2)[N:10]=1)=[O:3].O1CCOCC1.[ClH:39]>>[ClH:39].[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[N:10]=[C:9]([CH2:8][O:7][C:6]3[C:5]([F:32])=[C:4]([C:2]([NH2:1])=[O:3])[C:30]([F:31])=[CH:29][CH:28]=3)[O:13][N:12]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59402710HCID 59402710, compound

Product 1

HCID 66620348HCID 66620348, compoundYield 43%

Procedure

tert-Butyl N-[4-(5-[3-(aminocarbonyl)-2,4-difluorophenoxy]methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamate (300 mg, 0.67 mmol, 1 equiv.) was dissolved in 4N HCl in dioxane (7 ml, 28 mmol, 42 equiv.) and the reaction mixture was stirred at r.t. overnight. Volatiles were removed under reduced pressure, the residue was triturated with dry Et2O and the solid formed was filtered and rinsed with dry Et2O. The crude product (200 mg) was taken-up in EtOH (2 ml) and was triturated with 2N HCl in Et2O solution (0.3 ml) and dry Et2O. The white solid was filtered and washed with dry Et2O, to give 110 mg of the desired product (43% yield). HPLC-MS (method 1): m/z 347 [M+H-HCl]+, Rt=2.98 min.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue was triturated with dry Et2O
  3. customthe solid formed
  4. filtrationwas filtered
  5. washrinsed with dry Et2O
  6. customwas triturated with 2N HCl in Et2O solution (0.3 ml) and dry Et2O
  7. filtrationThe white solid was filtered
  8. washwashed with dry Et2O

Sources & evidence

ORD record
ord-62cd3fcef4dc4c23a27a5cf6293520bc
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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