Acryloyl chloride → HCID 67336899, compound

HRID 1675238Notes

Reaction equation

HRID 1675238 reaction equation
[NH2:1][C@@H:2]([CH3:42])[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][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[N:12]=[CH:11][N:10]=[C:9]2[NH:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[C:29]([Cl:41])[CH:28]=1)=[O:4].[C:43](Cl)(=[O:46])[CH:44]=[CH2:45].C(=O)(O)[O-].[Na+]>C1COCC1.O>[Cl:41][C:29]1[CH:28]=[C:27]([NH:26][C:9]2[C:8]3[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[C:6]([NH:5][C:3]([C@@H:2]([NH:1][C:43](=[O:46])[CH:44]=[CH2:45])[CH3:42])=[O:4])[CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:32]=[CH:31][C:30]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1

Participants

6

Reactant 3

HCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 67336198HCID 67336198, compound

Product 1

HCID 67336899HCID 67336899, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 mg of (2S)-2-amino-N-{4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl}-propionamide as a starting material was dissolved in 12 ml of THF and 4 ml of water, and reacted with 0.08 ml of acryloylchloride at room temperature for 1.5 hours after adding 213 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 (180 mg, 33%).

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-4739ff3c3a094a49a69b5693600d2fb8
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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