Water → HCID 67509998, compound

HRID 1747004Notes

Reaction equation

HRID 1747004 reaction equation
[NH2:1][C:2](=[O:36])[C:3](=[O:35])[CH:4]([NH:13][C:14](=[O:34])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[N:22]1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.Br[CH2:38][CH2:39][OH:40].N12CCCN=C1CCCCC2.O>CN(C)C=O>[NH2:1][C:2]([C:3]1([CH:4]([NH:13][C:14](=[O:34])[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][C:16]=2[N:21]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])=[N:22]2)[CH2:5][C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)[O:40][CH2:39][CH2:38][O:35]1)=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66720162HCID 66720162, compound

Product 1

HCID 67509998HCID 67509998, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[3-amino-1-(4-fluorobenzyl)-2,3-dioxopropyl]-2-[3-(2,4-dichlorophenyl)-1H-pyrazol-1-yl]nicotinamide (0.09 g, 0.171 mmol) was dissolved in dimethylformamide (DMF, 1.7 ml) forming a slight yellow solution. Then, 2-bromoethanol (0.059 ml, 0.838 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.090 ml, 0.598 mmol) were added with stirring at room temperature. Stirring was continued over night. Water was added to reaction mixture resulting in precipitation of the desired product. The suspension was stirred for 30 min. at 0-5° C. The suspension was filtered under reduced pressure, the precipitate washed three times with ice cold water, and subsequently dried at 40° C. under reduced pressure. The remaining residue (85 mg) was treated with a dichloromethane/methanol mixture (97:3 v/v) and the resulting suspension was stirred at room temperature for 30 min. The precipitate was filtered under reduced pressure. washed with few amounts of dichloromethane and subsequently dried at 40° C. under reduced pressure resulting in 19 mg off-white powder. An additional amount of pure desired product could be obtained by column chromatography of the evaporated filtrate.

Workup

  1. customforming a slight yellow solution
  2. stirringStirring
  3. waitwas continued over night

Sources & evidence

ORD record
ord-62bbb49bffbb4eefab9b74a0c7f825ca
Source dataset
uspto-grants-2015_10
Patent number
US09150553B2

Reaction notes

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