Ammonia → 5-(3-Methyl-[1,2,4]oxadiazol-5-yl)-4-phenyl-thiazol-2-ylamine

HRID 604490Notes

Reaction equation

HRID 604490 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([C:19]2[O:23][N:22]=[C:21]([CH3:24])[N:20]=2)=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O.N>C(O)(=O)C.[Cl-].[Na+].O>[CH3:24][C:21]1[N:20]=[C:19]([C:10]2[S:9][C:8]([NH2:7])=[N:12][C:11]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:23][N:22]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 57709599[5-(3-Methyl-[1,2,4]oxadiazol-5-yl)-4-phenyl-thiazol-2-yl]-carbamic Acid tert-butyl ester

Product 1

HCID 577095965-(3-Methyl-[1,2,4]oxadiazol-5-yl)-4-phenyl-thiazol-2-ylamineYield 98%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

[5-(3-Methyl-[1,2,4]oxadiazol-5-yl)-4-phenyl-thiazol-2-yl]-carbamic acid tert-butyl ester was suspended in glacial acetic acid (20 mL). TFA (20 mL) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was added to brine (100 mL) and pH was adjusted to pH 10 with ammonia. The mixture was extracted with EtOAc (2×75 mL). The combined organic phases was washed with brine (50 mL), dried with MgSO4 and solvents were removed in vacuo to give a white solid. Yield 98%.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×75 mL)
  2. washThe combined organic phases was washed with brine (50 mL)
  3. dry with materialdried with MgSO4 and solvents
  4. customwere removed in vacuo
  5. customto give a white solid

Sources & evidence

ORD record
ord-dfbcf9733a9c4367b58c1bd176115307
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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