HCID 178449572, compound → HCID 178514088, compound

HRID 1845777Notes

Reaction equation

HRID 1845777 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([NH:12][C:13]([NH:15][CH2:16][C:17]1[C:18]([C:22](=[N:32][OH:33])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([Cl:31])[CH:25]=2)=[N:19][O:20][N:21]=1)=[O:14])(C)(C)C>C(O)(C(F)(F)F)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:12][C:13]([NH:15][CH2:16][C:17]1[C:18]([C:22](=[N:32][OH:33])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([Cl:31])[CH:25]=2)=[N:19][O:20][N:21]=1)=[O:14]

Participants

3

Reactant 1

HCID 178449572HCID 178449572, compound

Product 1

HCID 178514088HCID 178514088, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-([(tert-Butylamino)carbonyl]aminomethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide trifluoroacetate (10 mg, 0.02 mmol) was stirred in TFA (2.0 mL) for 2 hrs. The reaction was warmed gently with heat gun. Evaporation and purification by preparative LCMS gave the desired product (8 mg, 70%). MF=C1IH13ClFN6O3; LCMS calculated for C11H11ClFN6O3(M+H)+: m/z=329.0. 1H NMR (400 MHz, CD3OD): δ 7.01 (m, 2H), 6.85 (m, 1H), 4.59 (s, 2H).

Workup

  1. temperatureThe reaction was warmed gently
  2. temperaturewith heat gun
  3. customEvaporation and purification by preparative LCMS

Sources & evidence

ORD record
ord-6dbc0821984645d489fe1dda86988461
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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