Dimethylformamide → HCID 67515574, compound

HRID 2092523Notes

Reaction equation

HRID 2092523 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[NH:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[C:4]([F:21])[CH:3]=1.[CH3:22][N:23](C=O)[CH3:24].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([N:23]([CH3:24])[CH3:22])=[O:17])=[CH:18][CH:19]=2)=[C:4]([F:21])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 61182641HCID 61182641, compound

Product 1

HCID 67515574HCID 67515574, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[3-(4-bromo-2-fluoro-phenyl)-ureido]-benzoic acid (0.5 g, 0.014 mol) in DMF (5 mL) N,N-dimethylamine hydrochloride (0.14 g, 0.0017 mol), HOBt (0.25 g, 0.0.0018 mol), EDC.HCl (0.41 g, 0.0021 mol) and TEA (0.4 mL, 0.0028 mol) were added. The reaction mixture was stirred at room temperature for 10 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×15 mL). The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford the title compound [0.33 g, 65%]; LC-MS (ESI): Calculated mass: 379.0; Observed mass: 382.0 [M+H] (RT: 1.41 min).

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b63f4421bb874226befaa4ecf73f48f3
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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