Triethylamine → 3-[5-Amino-4-(2-chlorobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide

HRID 1959513Notes

Reaction equation

HRID 1959513 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6](=[CH:9]NC1C=CC=CC=1)[C:7]#[N:8])=[O:5].FC(F)(F)C(O)=O.[CH:28]1([NH:31][C:32](=[O:42])[C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([NH:40][NH2:41])[CH:34]=2)[CH2:30][CH2:29]1.C(N(CC)CC)C>C(O)C>[NH2:8][C:7]1[N:40]([C:35]2[CH:34]=[C:33]([CH:38]=[CH:37][C:36]=2[CH3:39])[C:32]([NH:31][CH:28]2[CH2:30][CH2:29]2)=[O:42])[N:41]=[CH:9][C:6]=1[C:4](=[O:5])[C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 670242032-(2-Chlorobenzoyl)-3-phenylaminoacrylonitrileHCID 67024207N-cyclopropyl-3-hydrazinyl-4-methylbenzamide 2,2,2-trifluoroacetate

Product 1

HCID 113268833-[5-Amino-4-(2-chlorobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamideYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-chlorobenzoyl)-3-phenylaminoacrylonitrile (93 mg, 0.33 mmol, 1.0 eq), N-cyclopropyl-3-hydrazino-4-methylbenzamide trifluoroacetate (104 mg, 0.33 mmol, 1 eq), and triethylamine (31 μL, 0.22 mmol, 1.0 eq) in 20 mL of ethanol was heated to 60° C. for 48 h. After cooling, the mixture was concentrated and the residue was dissolved in minimal ethyl acetate. 100 ml diethyl ether was added and the precipitate was filtered and dried to provide desired product (50 mg, 39%). HPLC (4 minute 10-90 gradient) tR 2.51 min; MS m/z 395.1 [M+H]+; 1H NMR (DMSO), δ 8.50 (d, J=3.8 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.84 (s, 1H), 7.57 (m, 5H) 7.32 (s, 1H), 7.01 (s, 2H) 3.37 (m, 2H), 2.86 (m, 1H), 2.14 (s, 3H), 1.09 (t, 2H), 0.68 (m, 2H), 0.58 (m, 2H) ppm

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. dissolutionthe residue was dissolved in minimal ethyl acetate
  4. addition100 ml diethyl ether was added
  5. filtrationthe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-07c9c9751de643439fef6e3dd3a5ed92
Source dataset
uspto-grants-2013_04
Patent number
US08410160B2

Reaction notes

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