Triethylamine → HCID 68536987, compound

HRID 1993708Notes

Reaction equation

HRID 1993708 reaction equation
Cl.[F:2][CH2:3][C:4]([C:8]1[CH:9]=[C:10]([NH:20][C:21]([NH:23][C:24]2[C:25]([CH3:36])=[N:26][C:27]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:28][CH:29]=2)=[O:22])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:12]=1)([CH2:6][F:7])[CH3:5].[F:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:39]=1[C:40](Cl)=[O:41].C(N(CC)CC)C>C(Cl)Cl>[F:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:39]=1[C:40]([N:33]1[CH2:32][CH2:31][N:30]([C:27]2[N:26]=[C:25]([CH3:36])[C:24]([NH:23][C:21]([NH:20][C:10]3[N:11]([C:13]4[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=4)[N:12]=[C:8]([C:4]([CH2:6][F:7])([CH3:5])[CH2:3][F:2])[CH:9]=3)=[O:22])=[CH:29][CH:28]=2)[CH2:35][CH2:34]1)=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 68535206HCID 68535206, compound

Product 1

HCID 68536987HCID 68536987, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir 1-[5-(2-Fluoro-1-fluoromethyl-1-methyl-ethyl)-2-p-tolyl-2H-pyrazol-3-yl]-3-(2-methyl-6-piperazin-1-yl-pyridin-3-yl)-urea hydrochloride (0.85 mmol, 0.5 g), 2,6-difluorobenzoyl chloride (0.85 mmol, 0.1 mL) and triethylamine (2.6 mmol, 0.4 mL) in 5 mL of CH2Cl2 at room temperature overnight. Add water and extract in CH2Cl2. Wash organic layer with saturated aq. sodium chloride solution. Dry over anhydrous sodium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with using hexanes/ethyl acetate (20%-70%). MS(ES): m/z=624 [M+H].

Workup

  1. extractionAdd water and extract in CH2Cl2
  2. dry with materialDry over anhydrous sodium sulfate
  3. concentrationconcentrate under reduced pressure
  4. washSubject residue to silica gel chromatography eluting with using hexanes/ethyl acetate (20%-70%)

Sources & evidence

ORD record
ord-89d18020cf8d46949dbc8d23a38c4a0f
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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