Acryloyl chloride → HCID 67334298, compound

HRID 1675236Notes

Reaction equation

HRID 1675236 reaction equation
[NH2:1][C@@H:2]([CH3:35])[C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1OCC)[N:12]=[CH:11][N:10]=[C:9]2[NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[C:22]([Cl:34])[CH:21]=1)=[O:4].[C:36](Cl)(=[O:39])[CH:37]=[CH2:38].[C:41](=O)(O)[O-:42].[Na+]>C1COCC1.O>[Cl:34][C:22]1[CH:21]=[C:20]([NH:19][C:9]2[C:8]3[C:13](=[CH:14][C:15]([O:42][CH3:41])=[C:6]([NH:5][C:3]([C@@H:2]([NH:1][C:36](=[O:39])[CH:37]=[CH2:38])[CH3:35])=[O:4])[CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:25]=[CH:24][C:23]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

6

Reactant 3

HCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 67334544HCID 67334544, compound

Product 1

HCID 67334298HCID 67334298, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

300 mg of (2S)-amino-N-{4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-7-ethoxy-quinazolin-6-yl}-propionamide as a starting material was dissolved in 9 ml of THF and 3 ml of water, and reacted with 0.06 ml of acryloylchloride at room temperature for 1 hour after adding 153 mg of sodium bicarbonate. The reacted solution was extracted with a mixture of chloroform and isopropanol after adding water, washed with saturated saline solution, dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure, and the resulting residue was subjected to column chromatography (eluent-ethylacetate:methanol=15:1) to obtain the title compound (11 mg, 3%).

Workup

  1. extractionThe reacted solution was extracted with a mixture of chloroform and isopropanol
  2. additionafter adding water
  3. washwashed with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-179c0701db47484dbc4aa45f8b614bc8
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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