Triethylamine → methyl 3-((4-(piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)carbamoyl)benzoate

HRID 926888Notes

Reaction equation

HRID 926888 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:8]=1)=[O:5].C(N(CC)CC)C.Cl[C:40]([C:42]1[CH:43]=[C:44]([CH:49]=[CH:50][CH:51]=1)[C:45]([O:47][CH3:48])=[O:46])=[O:41]>ClCCl>[N:26]1([C:23]2[CH:24]=[CH:25][C:2]([NH:1][C:40]([C:42]3[CH:43]=[C:44]([CH:49]=[CH:50][CH:51]=3)[C:45]([O:47][CH3:48])=[O:46])=[O:41])=[C:3]([C:4](=[O:5])[NH:6][C:7]3[CH:11]=[CH:10][N:9]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=4)[N:8]=3)[CH:22]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15563901Methyl 3-(chlorocarbonyl)benzoateHCID 665874172-amino-5-(piperidin-1-yl)-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamide

Product 1

HCID 66587449methyl 3-((4-(piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)carbamoyl)benzoateYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 100-mL 3-necked round bottom flask, was placed a solution of 2-amino-5-(piperidin-1-yl)-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamide (260 mg, 0.61 mmol, 1.00 equiv) in dichloromethane (20 mL), and triethylamine (123 mg, 1.22 mmol, 2.01 equiv). This was followed by dropwise addition of a solution of methyl 3-(chlorocarbonyl)benzoate (144 mg, 0.73 mmol, 1.20 equiv) in dichloromethane (10 mL) with stirring at 0° C. The resulting solution was stirred for 2 h at room temperature, with reaction progress monitored by LCMS. The resulting mixture was washed with 3×20 mL of water and 20 mL of brine, then dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum to give 300 mg of crude product as a brown solid.

Workup

  1. customInto a 100-mL 3-necked round bottom flask, was placed
  2. stirringThe resulting solution was stirred for 2 h at room temperature, with reaction progress
  3. washThe resulting mixture was washed with 3×20 mL of water and 20 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-8692d62c6e694e0facb280785ee491ca
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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