Formate → HCID 59587546, compound

HRID 389713Notes

Reaction equation

HRID 389713 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=2[F:31])[O:7][C:8]=1[C:9]1[CH:23]=[CH:22][C:12]([CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:11][CH:10]=1)(=[O:3])[NH2:2].Cl.O1CCOCC1.C([O-])=O>C(Cl)Cl>[NH2:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([C:8]2[O:7][C:6]([C:24]3[C:25]([F:31])=[CH:26][CH:27]=[CH:28][C:29]=3[F:30])=[N:5][C:4]=2[C:1]([NH2:2])=[O:3])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 283FormateHCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59587479HCID 59587479, compound

Product 1

HCID 59587546HCID 59587546, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-carbamoyl-2-(2,6-difluorophenyl)oxazol-5-yl)benzylcarbamate (0.110 g, 0.26 mmol) in DCM (10 mL) was added 4M HCl in dioxane (1.5 mL, 6.0 mmol) and the resulting mixture stirred at room temperature overnight. The solvent was then removed in vacuo. The residue was purified by preparative HPLC to afford 5-(4-(aminomethyl)phenyl)-2-(2,6-difluorophenyl)oxazole-4-carboxamide (0.0366 g, 0.11 mmol, 43%) as a white solid as the formate salt. 1H NMR (DMSO) 3.95 (2H, s), 7.40 (2H, t), 7.55 (2H, d), 7.74 (3H, m), 8.21 (2H, d), 8.33 (1H, s). LCMS (2) Rt: 2.30 min; m/z (ES+) 330.

Workup

  1. customThe solvent was then removed in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1ae8f9a5bf25485e85a3fcc7058b5cec
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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