1,2-Dichloroethane → HCID 178522448, compound

HRID 659776Notes

Reaction equation

HRID 659776 reaction equation
CO[C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-].[Na+].[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([C:31]2[C:35]([NH2:36])=[CH:34][NH:33][N:32]=2)=[O:30])=[CH:24][CH:23]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O.O>[F:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:29]([C:31]2[C:35]([NH:36][C:3](=[O:18])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)=[CH:34][NH:33][N:32]=2)=[O:30])=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 59733402Methyl 2-(2-(pyrrolidin-1-yl)ethoxy)benzoateHCID 178508056HCID 178508056, compound

Product 1

HCID 178522448HCID 178522448, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

2-(2-Pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester (0.104 g, 0.42 mmol) was treated with 2 M aqueous NaOH (20 ml) and water (20 ml). The reaction mixture was stirred at room temperature for 20 hours, then reduced in vacuo and azeotroped with toluene (3×5 ml). Water (50 ml) was added and the mixture taken to pH 5 using 1M aqueous HCl. The resulting solution was reduced in vacuo and azeotroped with toluene (3×5 ml) to give a white solid, which was combined with 4-amino-1H-pyrazole-3-carboxylic acid (4-fluoro-phenyl)-amide (Example 2B) (0.055 g, 0.25 mmol), EDC (0.058 g, 0.3 mmol) and HOBt (0.041 g, 0.3 mmol) and stirred at room temperature in DMSO (3 ml) for 20 hours. The reaction mixture was poured into water (30 ml) and the resultant solid was collected by filtration and dried in a vacuum oven to give the title compound as a grey solid (0.015 g, 14%). (LC/MS: Rt 2.18, [MH]+ 438.06).

Workup

  1. customazeotroped with toluene (3×5 ml)
  2. additionWater (50 ml) was added
  3. customazeotroped with toluene (3×5 ml)
  4. customto give a white solid, which
  5. filtrationthe resultant solid was collected by filtration
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-1abeb784937c4266a0f0cbc333d49d50
Source dataset
uspto-grants-2011_12
Patent number
US08080666B2

Reaction notes

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