4-Methylbenzoyl Chloride → HCID 21076931, compound

HRID 1455160Notes

Reaction equation

HRID 1455160 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=O)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH2:20]([N:27]1[C:32](=[O:33])[C:31]([CH3:34])=[C:30]([CH3:35])[N:29]=[C:28]1[C@H:36]([NH:40][CH2:41][CH2:42][N:43]1C(=O)C2C(=CC=CC=2)C1=O)[CH:37]([CH3:39])[CH3:38])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1>[CH2:20]([N:27]1[C:32](=[O:33])[C:31]([CH3:34])=[C:30]([CH3:35])[N:29]=[C:28]1[C@H:36]([N:40]1[CH2:41][CH2:42][N:43]=[C:7]1[C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)[CH:37]([CH3:39])[CH3:38])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 134054-Methylbenzoyl ChlorideHCID 81531DiisopropylethylamineHCID 21226206Ethyl acetate hexaneHCID 69085270HCID 69085270, compound

Product 1

HCID 21076931HCID 21076931, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

p-Toluoyl chloride (0.033 mL, 0.25 mMol) was dissolved in toluene (2 mL) and was treated with DIPEA (0.093 mL, 0.53 mMol) followed by 2-{2-[(R)-1-(1-benzyl-4,5-dimethyl-6-oxo-1,6-dihyro-pyrimidin-2-yl)-2-methyl-propylamino]-ethyl}-isoindole-1,3-dione (0.100 g, 0.22 mMol) The reaction stirred at 110° C. for 3 h. The reaction was cooled to room temperature and was evaporated under reduced pressure and purified by flash chromatography. (EtOAc/hexane 0-55% gradient) to give the title compound 0.075 g (0.13 mMol) MS (ES) m/e 577 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customwas evaporated under reduced pressure
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-cdac6a0474324a65bb91565c9df29daa
Source dataset
uspto-grants-2009_01
Patent number
US07482343B2

Reaction notes

Loading…