Sodium Hydroxide → HCID 178449572, compound

HRID 2097648Notes

Reaction equation

HRID 2097648 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][C:10]1[C:11]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)C(=O)[O:17][N:16]=2)=[N:12][O:13][N:14]=1.[N:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[C:30]=[O:31].[OH-].[Na+]>C(Cl)Cl.O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:32]([NH:29][C:30]([NH:8][CH2:9][C:10]1[C:11]([C:15](=[N:16][OH:17])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=2)=[N:12][O:13][N:14]=1)=[O:31])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 62412tert-Butyl isocyanateHCID 69266958HCID 69266958, compound

Product 1

HCID 178449572HCID 178449572, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one trifluoroacetate (15 mg, 0.035 mmol) and TEA (15 μL, 0.10 mmol) were dissolved in DCM (0.5 mL) and then 2-isocyanato-2-methylpropane (24 μL, 0.21 mmol) was added. The reaction was stirred for 16 h at room temperature. A solution of sodium hydroxide in water (0.50 mL, 1.0 N) was added and the mixture stirred at room temperature for 2 h. Acidification with acetic acid and purification by preparative LCMS gave the desired product (12 mg, 68%). MF═C15H18ClFN6O3; LCMS calculated for C15H19ClFN6O3 (M+H)+: m/z=385.0.

Workup

  1. stirringthe mixture stirred at room temperature for 2 h
  2. customAcidification with acetic acid and purification by preparative LCMS

Sources & evidence

ORD record
ord-ee54b8f173ce4127890121525e875b13
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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