Water → HCID 59504732, compound

HRID 2400593Notes

Reaction equation

HRID 2400593 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:41]=[CH:40][C:23]([CH2:24][N:25](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:22][CH:21]=3)[N:16]=2)[CH:3]=1.FC(F)(F)C(O)=O.O>ClCCl>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[CH:22][C:23]([CH2:24][NH2:25])=[CH:40][CH:41]=3)[N:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 59504734HCID 59504734, compound

Product 1

HCID 59504732HCID 59504732, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred solution of di-tert-butyl (4-{5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazol-3-yl}benzyl)imidodicarbonate (Example 98, 2.73 g, 4.88 mmol) in dichloromethane (37 mL) was added trifluoroacetic acid (3.7 mL, 48.8 mmol). After the reaction mixture had been stirred at rt for 3 h, water (50 mL) was added, and it was extracted with dichloromethane (3×30 mL). The aqueous phase was then made alkaline (pH 10) by addition of potassium carbonate. It was extracted with dichloromethane (3×30 mL). The combined organic extracts were dried over anhydrous sodium sulfate. After filtration and evaporation of the solvent, the title compound was obtained (1.28 g, 73%): 1H NMR (400 MHz, DMSO-d6) 8.02 (d, 2H), 7.55 (d, 2H), 7.18 (d, 2H), 7.11 (d, 2H), 6.90 (s, 1H), 5.43 (s, 2H), 3.85 (s, 2H), 2.32 (s, 3H), 2.28 (s, 3H); ES-MS m/z 360, HPLC RT (Method D) 1.56 min.

Workup

  1. extractionit was extracted with dichloromethane (3×30 mL)
  2. additionby addition of potassium carbonate
  3. extractionIt was extracted with dichloromethane (3×30 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-bfe112ad2b5a47b2861e424cd82b91b0
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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