Water → HCID 19603289, compound

HRID 1604560Notes

Reaction equation

HRID 1604560 reaction equation
[Cl:1][C:2]1[C:20]([N:21]([CH3:38])[C:22](=[O:37])[CH2:23][NH:24][C:25](=[O:36])/[CH:26]=[CH:27]/[C:28]2[CH:29]=[N:30]C(NC)=C[CH:33]=2)=[CH:19][CH:18]=[C:17]([Cl:39])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.[CH2:40]([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])C.C(Cl)(=[O:49])C.O>ClCCl>[Cl:1][C:2]1[C:20]([N:21]([CH3:38])[C:22](=[O:37])[CH2:23][NH:24][C:25](=[O:36])/[CH:26]=[CH:27]/[C:28]2[CH:29]=[N:30][C:43]([N:42]([CH3:40])[C:45](=[O:49])[CH3:46])=[CH:44][CH:33]=2)=[CH:19][CH:18]=[C:17]([Cl:39])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19603284HCID 19603284, compound

Product 1

HCID 19603289HCID 19603289, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-[2,6-dichloro-3-[N-methyl-N-[(E)-3-(6-methylaminopyridin-3-yl)acryloylglycyl]amino]benzyloxy]-2-methylquinoline (100 mg) and triethylamine (23.3 mg) in dichloromethane was added acetyl chloride (15.3 mg) under nitrogen in ice water bath, and the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1, V/V) to give 8-[2,6-dichloro-3-[N-methyl-N[(E)-3-[6-(N-methylacetamido)pyridin-3-yl]acryloylglycyl]amino]-benzyloxy]-2-methylquinoline (50 mg) as an amorphous powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1, V/V)

Sources & evidence

ORD record
ord-a509d4d81442443da25a6231b4dbfa98
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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