Thiophene → HCID 13851198, compound

HRID 978457Notes

Reaction equation

HRID 978457 reaction equation
Cl.Cl.NC1[CH:13]=[C:12]2C([C:8](=[O:32])[N:9]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([C:23](=[O:31])[C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[CH2:19][CH2:18]3)[C:10](=[O:14])[NH:11]2)=CC=1.C([O-])(=O)C.[K+].S1[CH:42]=[CH:41][CH:40]=[CH:39]1.[H][H].[CH3:45][N:46](C)[C:47](=O)C>CO.[Pd].COCCO>[CH3:45][N:46]([CH3:47])[C:39]1[CH:13]=[C:12]2[C:42]([C:8](=[O:32])[N:9]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([C:23](=[O:31])[C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[CH2:19][CH2:18]3)[C:10](=[O:14])[NH:11]2)=[CH:41][CH:40]=1

Participants

10

Reactant 6

HCID 8030ThiopheneHCID 31374DimethylacetamideHCID 517044Potassium AcetateHCID 20202892HCID 20202892, compoundHCID 178418361HCID 178418361, compoundHCID 178486302HCID 178486302, compound

Product 1

HCID 13851198HCID 13851198, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.85 parts of 7-amino-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione dihydrochloride, 4 parts of potassium acetate, 300 parts of 2-methoxyethanol, 1 part of a solution of thiophene in methanol 4% and 4 parts of poly(oxymethylene) was hydrogenated at normal pressure and at 60° C. with 2 parts of palladium-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up (about 8 days), the reaction mixture was diluted with 270 parts of N,N-dimethylacetamide and heated to 100° C. The catalyst was filtered off over diatomaceous earth. The filtrate was stirred and cooled and 100 parts of water were added. The precipitated product was filtered off, washed with water and stirred in 2-propanone. The product was filtered off and dried, yielding 2.3 parts (52%) of 7-(dimethylamino)-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H ,3H)-quinazolinedione; mp. 300° C. (31).

Workup

  1. custom(about 8 days)
  2. filtrationThe catalyst was filtered off over diatomaceous earth
  3. temperaturecooled
  4. addition100 parts of water were added
  5. filtrationThe precipitated product was filtered off
  6. washwashed with water
  7. stirringstirred in 2-propanone
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-f96eeb3b64414a819adcb750af7544f6
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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