Triethylamine → {{8-[5-(4-Fluorophenyl)-2-pentyl]-10-hydroxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl}acetyl}urea

HRID 427093Notes

Reaction equation

HRID 427093 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH:19]([C:21]2[CH:26]=[C:25]([OH:27])[C:24]3[C:28]4[CH2:29][NH:30][CH2:31][CH2:32][C:33]=4[C:34]([CH3:37])([CH3:36])[O:35][C:23]=3[CH:22]=2)[CH3:20])=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH:19]([C:21]2[CH:26]=[C:25]([OH:27])[C:24]3[C:28]4[CH2:29][N:30]([CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4])[CH2:31][CH2:32][C:33]=4[C:34]([CH3:36])([CH3:37])[O:35][C:23]=3[CH:22]=2)[CH3:20])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78516(2-Chloroacetyl)ureaHCID 128007415,5-dimethyl-8-[5-(4-fluorophenyl)-2-pentyl]-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine

Product 1

HCID 44327286{{8-[5-(4-Fluorophenyl)-2-pentyl]-10-hydroxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl}acetyl}urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.50 g. (0.011 mole) of chloroacetyl urea in 20 ml. of dimethylformamide was added dropwise to a stirred solution of 3.95 g. (0.01 mole) of 8-[5-(4-fluorophenyl)-2-pentyl]-10-hydroxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridine in 25 ml. of dimethylformamide and 1.11 g. (0.011 mole) of triethylamine. After stirring at room temperature for 22 hours, the mixture was diluted with 45 ml. of water and extracted with ether. The combined ether extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was recrystallized from acetonitrile, m.p. 133°-134°.

Workup

  1. additionthe mixture was diluted with 45 ml
  2. extractionof water and extracted with ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from acetonitrile, m.p. 133°-134°

Sources & evidence

ORD record
ord-0f8f54fdfea04215a741ec2ea6cace57
Source dataset
uspto-grants-1979_10
Patent number
US04172943

Reaction notes

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