Potassium Carbonate → HCID 10578517, compound

HRID 1839440Notes

Reaction equation

HRID 1839440 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[C:10]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:7])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:38][C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40]>CC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[C:10]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[CH:11][C:12]([O:15][CH2:38][C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 11795219HCID 11795219, compound

Product 1

HCID 10578517HCID 10578517, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of N1-(3-cyanobenzoyl)-N2-(4-isopropylbenzoyl)-4-hydroxy-1,2-benzenediamine (502 mg, 1.26 mmol), acetone (15 mL), and potassium carbonate (216 mg, 1.56 mmol) was added by benzyl 2-bromoacetate (0.4 mL, 2.52 mmol). After stirring overnight, the reaction was concentrated and the residue was chromatographed (100% CH2Cl2 to 10% EtOAc/CH2Cl2) to give the title compound as a solid (532 mg, 77%), IR(CHCl3): 2965, 1759, 1654, 1610, 1514, 1175 cm−1; NMR(300 MHz, CDCl3): δ1.28 (s, 3H), 1.30 (s, 3H), 3.00 (m, 1H), 4.50 (s, 2H), 5.22 (s, 2H), 6.71 (d, 1H, J=9.3), 6.93 (s, 1H), 7.31 (m, 7H), 7.54 (d, 1H, J=21), 7.60 (t, 1H, J=7.8), 7.78 (d, 1H, J=8.7), 7.89 (d, 2H, J=8.1), 8.19 (d, 1H, J=8.1), 8.30 (s, 1H), 8.74 (br s, 1H), 9.48 (br s, 1H); MS(FD): 547.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was chromatographed (100% CH2Cl2 to 10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-2633a76260d84ca7b7e234a3d63f9a14
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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