Dimethylamine → HCID 59631970, compound

HRID 2369089Notes

Reaction equation

HRID 2369089 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=2)=[CH:11][C:10]([C:22]([F:25])([F:24])[F:23])=[N:9]1.[CH3:26][NH:27][CH3:28].C(N(CC)C(C)C)(C)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([N:27]([CH3:28])[CH3:26])=[O:18])=[CH:15][CH:14]=2)=[CH:11][C:10]([C:22]([F:25])([F:24])[F:23])=[N:9]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 86649377HCID 86649377, compound

Product 1

HCID 59631970HCID 59631970, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 1 dram vial was added 4-[2-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-benzoyl chloride (300 mL, 0.3 mmol) as a 0.1M solution in Dichloromethane, Dimethyl-amine (27 mg, 0.6 mmol) and N,N-Diisopropylethylamine (77.4 mg, 0.6 mmol). The reaction was stirred at room temperature for 30 min and then placed directly on silica and purified using a gradient of Hexane to Ethyl Acetate 0-50% over 10 CV. The relevant fractions were combined and dried in vacuo to give 108.6 mg (92%) of an off white solid; MS (ES): 394 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 7.84 (dd, J=7.8 Hz; 1.7 Hz 1H), 7.73-7.58 (m, 3H), 7.45-7.35 (m, 5H), 3.00 (s, 3H), 2.89 (s, 3H).

Workup

  1. custompurified
  2. customdried in vacuo
  3. customto give 108.6 mg (92%) of an off white solid

Sources & evidence

ORD record
ord-3697087822094f55ad8783b57bef117b
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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