4-Bromobenzoic acid → HCID 16894700, compound

HRID 737095Notes

Reaction equation

HRID 737095 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.C1([CH:18]2[CH2:23][O:22][CH2:21][CH2:20][NH:19]2)C=CC=CC=1.[CH:24]1[CH:25]=[CH:26][C:27]2N(O)N=N[C:28]=2[CH:29]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(Cl)CCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:19]2[CH2:20][CH2:21][O:22][CH:23]([C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:29]=3)[CH2:18]2)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 114644-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 177498203-Phenylmorpholine--hydrogen chloride (1/1)

Product 1

HCID 16894700HCID 16894700, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5 g of p-Bromobenzoic acid, 4.966 g 3-Phenylmorpholine HCl, 5.245 g EDC, 3.696 g HOBt and 4.766 mL Hunig's Base in 25 mL DMF was stirred at room temperature overnight. The reaction was diluted with water and extracted with ethyl acetate. The organic layers were combined, washed with 1N HCl, aqueous saturated sodium bicarbonate solution and brine. The organics were concentrated in vacuo and purified by flash chromatography to afford product. Wt: 1.335 g, 77% yield. ES MS m/z 346/348

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with 1N HCl, aqueous saturated sodium bicarbonate solution and brine
  3. concentrationThe organics were concentrated in vacuo
  4. custompurified by flash chromatography
  5. customto afford product

Sources & evidence

ORD record
ord-2696da2a7b9a4a8e8c68460ba1242e9d
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

Loading…