Acryloyl chloride → HCID 67333814, compound

HRID 1675239Notes

Reaction equation

HRID 1675239 reaction equation
[NH2:1][C@@H:2]([CH3:38])[C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])[N:12]=[CH:11][N:10]=[C:9]2[NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[C:25]([Cl:37])[CH:24]=1)=[O:4].[C:39](Cl)(=[O:42])[CH:40]=[CH2:41].C(=O)(O)[O-].[Na+]>C1COCC1.O>[Cl:37][C:25]1[CH:24]=[C:23]([NH:22][C:9]2[C:8]3[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])=[C:6]([NH:5][C:3]([C@@H:2]([NH:1][C:39](=[O:42])[CH:40]=[CH2:41])[CH3:38])=[O:4])[CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

6

Reactant 3

HCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 67334144HCID 67334144, compound

Product 1

HCID 67333814HCID 67333814, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

400 mg of (2S)-2-amino-N-{4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-7-(3-methoxypropoxy)-quinazolin-6-yl}-propionamide as a starting material was dissolved in 10 ml of THF and 3 ml of water, and reacted with 0.07 ml of acryloylchloride at room temperature for 1.5 hours after adding 188 mg of sodium bicarbonate. The reacted solution was extracted with a mixture of chloroform and isopropanol after adding water, washed with water and 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 (110 mg, 25%).

Workup

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

Sources & evidence

ORD record
ord-523e87fc380345d0a7b8f595173f1b97
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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