Dimethylformamide → HCID 14998282, compound

HRID 1032616Notes

Reaction equation

HRID 1032616 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][C:5]2[CH:7]=[C:8]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=3)[CH:9]=[CH:10][C:4]=2[O:3]1.CN(C)C=O.C(N(CC)CC)C.[CH3:34][O:35][N:36]([CH3:40])[C:37](Cl)=[O:38]>O>[CH3:1][C:2]1([CH3:21])[CH2:6][C:5]2[CH:7]=[C:8]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:37]([N:36]([O:35][CH3:34])[CH3:40])=[O:38])=[CH:16][N:15]=3)[CH:9]=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 14998281HCID 14998281, compound

Product 1

HCID 14998282HCID 14998282, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.2 g of 2-[2-(2,3-dihydro-2,2-dimethyl-5-benzofuranyl)ethoxy]-5-aminopyridine was dissolved into 10 ml of N,N-dimethylformamide, and 0.9 g of triethylamine was added thereto. 1.2 g of N-methoxy-N-methylcarbamoyl chloride was slowly added dropwise thereto. After the mixture was stirred at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was dried off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (2/3) as a developer to obtain 2.1 g of 1-{2-[2-(2,3-dihydro-2,2-dimethyl-5-benzofuranyl)ethyloxy]-5-pyridyl}-3-methoxy-3-methylurea.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water, it
  4. dry with materialwas dried over anhydrous magnesium sulfate and ethyl acetate
  5. customwas dried off

Sources & evidence

ORD record
ord-4b58a5b6d8c44fc7813a1ef5915854c7
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

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