Dimethylformamide → HCID 20468178, compound

HRID 1903189Notes

Reaction equation

HRID 1903189 reaction equation
[CH3:1]N(C)C=O.[CH2:6]([N:13]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:14]1=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:33]([O:35][CH2:36][CH:37]([CH3:39])C)=O.[CH2:40]([NH:42][CH2:43]C1CCCCO1)[CH3:41]>CO.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:6]([N:13]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([N:42]([CH2:43][CH:36]3[CH2:37][CH2:39][CH2:1][CH2:33][O:35]3)[CH2:40][CH3:41])=[O:30])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:14]1=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62365Isobutyl chloroformateHCID 13288216N-[(Oxan-2-yl)methyl]ethanamineHCID 20467955HCID 20467955, compound

Product 1

HCID 20468178HCID 20468178, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Into 100 ml of dimethylformamide were added 3.1 g of 1-benzyl-6-(4-carboxybutoxy)-3,4-dihydrocarbostyril and 1.7 ml of triethylamine. The outside of the reaction vessel containing the above mentioned mixture was ice-cooled and 1.4 ml of isobutyl chloroformate was added dropwise to the mixture under stirring condition. After the addition operation, stirring was continued for 30 minutes and 1.75 g of N-ethyl-N-(2-tetrahydropyranylmethyl)amine was added to the reaction mixture and further stirred at a room temperature for 3 hours. After the reaction was completed, the solvent was removed by distillation and the residue thus obtained was extracted with about 300 ml of chloroform and washed with a diluted NaHCO3 aqueous solution, water, a diluted hydrochloric acid and water in this order. The residue thus obtained was treated by silica-gel column chromatography (solvent used was a mixture of chloroform:methanol=20:1) and the elue thus obtained was concentrated to obtain 2.3 g of 1-benzyl-6-{4-[N-(2-tetrahydropyranylmethyl)-N-ethylaminocarbonyl]butoxy}-3,4-dihydrocarbostyril in the form of a colorless syrupy substance.

Workup

  1. additionThe outside of the reaction vessel containing the
  2. temperaturecooled
  3. stirringAfter the addition operation, stirring
  4. stirringfurther stirred at a room temperature for 3 hours
  5. customthe solvent was removed by distillation
  6. customthe residue thus obtained
  7. extractionwas extracted with about 300 ml of chloroform
  8. washwashed with a diluted NaHCO3 aqueous solution, water
  9. customThe residue thus obtained
  10. additionwas treated by silica-gel column chromatography (solvent
  11. concentrationwas concentrated

Sources & evidence

ORD record
ord-44a462f0b9df42c8811e2fbdc511fb5b
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

Loading…