Triethylamine → {[10-Hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]-alpha-methylacetyl}urea

HRID 427099Notes

Reaction equation

HRID 427099 reaction equation
Cl[CH:2]([CH3:9])[C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4].[OH:10][C:11]1[C:16]2[C:17]3[CH2:18][NH:19][CH2:20][CH2:21][C:22]=3[C:23]([CH3:26])([CH3:25])[O:24][C:15]=2[CH:14]=[C:13]([CH:27]([CH3:35])[CH:28]([CH3:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]=1.C(N(CC)CC)C>CN(C)C=O>[OH:10][C:11]1[C:16]2[C:17]3[CH2:18][N:19]([CH:2]([CH3:9])[C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4])[CH2:20][CH2:21][C:22]=3[C:23]([CH3:25])([CH3:26])[O:24][C:15]=2[CH:14]=[C:13]([CH:27]([CH3:35])[CH:28]([CH3:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2135435H-(1)Benzopyrano(4,3-c)pyridine, 1,2,3,4-tetrahydro-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-HCID 5150651(2-Chloro-propionyl)-urea

Product 1

HCID 20388007{[10-Hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]-alpha-methylacetyl}urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.66 g. (0.011 mole) of 2-chloropropionylurea in 20 ml. of dimethylformamide was added dropwise to a stirred solution of 3.57 g. (0.01 mole) of 10-hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridine in 20 ml. of dimethylformamide and 1.11 g. (0.011 mole) of triethylamine. The reaction mixture was stirred at room temperature for 72 hours, diluted with 60 ml. of water, and extracted with ether. The ether extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by chromatography on a 100-200 mesh Florisil activated magnesium silicate column and chloroform; m.p. 95°-100°.

Workup

  1. additiondiluted with 60 ml
  2. extractionof water, and extracted with ether
  3. washThe ether extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on a 100-200 mesh Florisil

Sources & evidence

ORD record
ord-b776e40d8d7d40d28356dc0687ce4535
Source dataset
uspto-grants-1979_10
Patent number
US04172943

Reaction notes

Loading…