Formate → HCID 59587370, compound

HRID 714949Notes

Reaction equation

HRID 714949 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[O:7][C:8]=1[C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)(=[O:3])[NH2:2].Cl.O1CCOCC1.C([O-])=O>C(Cl)Cl>[F:35][C:34]1[CH:33]=[CH:32][CH:31]=[C:30]([F:36])[C:29]=1[C:6]1[O:7][C:8]([C:9]2[CH:10]=[CH:11][C:12]([CH2:13][N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)=[CH:27][CH:28]=2)=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=1

Participants

6

Reactant 4

HCID 283FormateHCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59587593HCID 59587593, compound

Product 1

HCID 59587370HCID 59587370, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(4-carbamoyl-2-(2,6-difluorophenyl)oxazol-5-yl)benzyl)piperazine-1-carboxylate (0.100 g, 0.2 mmol) in DCM (3 mL) was added 4M HCl in dioxane (2 mL, 8.0 mmol) and the resulting mixture stirred at room temperature overnight. The solvent was removed in vacuo. The residue was purified by preparative HPLC to afford 2-(2,6-difluorophenyl)-5-(4-(piperazin-1-ylmethyl)phenyl)oxazole-4-carboxamide (0.043 g, 0.1 mmol, 50%) as a white solid as the formate salt. 1H NMR (DMSO) 2.44 (4H, m), 2.88 (4H, m), 3.55 (2H, s), 7.40 (2H, t), 7.47 (2H, d), 7.75 (3H, m), 8.19 (2H, d), 8.32 (1H, s). LCMS (2) Rt: 2.63 min; m/z (ES+) 399.

Workup

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

Sources & evidence

ORD record
ord-9543ee69804541e99a5cfa5744b49f03
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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