Triethylamine → HCID 59504757, compound

HRID 2400598Notes

Reaction equation

HRID 2400598 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:9]=[C:8]([CH3:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:6]=1)[NH2:4].C(N(CC)CC)C.[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=O)=[CH:31][CH:30]=1>ClCCl>[CH3:10][C:8]1[N:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:6]=[C:5]([C:3]2[N:4]=[C:33]([C:32]3[CH:36]=[CH:37][C:29]([O:28][C:27]([F:26])([F:38])[F:39])=[CH:30][CH:31]=3)[O:1][N:2]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 136633699HCID 136633699, compound

Product 1

HCID 59504757HCID 59504757, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred solution of N′-hydroxy-5-methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carboximidamide (Intermediate KK, 110 mg, 0.45 mmol) and triethylamine (188 μL, 1.35 mmol) in dichloromethane (4 mL) was added 4-(trifluoromethyoxy)benzoyl chloride (101 mg, 0.45 mmol) at a temperature of 0° C. After stirring at rt for 1 h, when analytical HPLC indicated complete conversion of the starting materials, all volatiles were removed in vacuo. The residue was re-dissolved in DMSO (6 mL) and heated to 140° C. for 30 minutes in a microwave oven (CEM Discover). Then, the reaction mixture was diluted with a few mL of methanol and subjected to preparative HPLC. The title compound was obtained in pure form (110 mg, 59%): 1H NMR (400 MHz, CDCl3) δ 8.32 (d, 2H), 7.37 (d, 2H), 7.12 (d, 2H), 7.05 (d, 2H), 6.71 (s, 1H), 5.40 (s, 2H), 2.31 (s, 3H), 2.23 (s, 3H); ES-MS m/z 415 (MH)+; HPLC RT (Method K) 1.58 min.

Workup

  1. customall volatiles were removed in vacuo
  2. dissolutionThe residue was re-dissolved in DMSO (6 mL)
  3. temperatureheated to 140° C. for 30 minutes in a microwave oven (CEM Discover)
  4. additionThen, the reaction mixture was diluted with a few mL of methanol

Sources & evidence

ORD record
ord-26b2e3b9c8b745f3bc600952dcfaa555
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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