Acetic Acid → HCID 13851173, compound

HRID 978451Notes

Reaction equation

HRID 978451 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][C:23]([N+:29]([O-])=O)=[CH:24][CH:25]=4)[NH:20][C:19]3=[O:32])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(O)(=O)C.S1C=CC=C1.[H][H]>CO.[Pd]>[NH2:29][C:23]1[CH:22]=[C:21]2[C:26]([C:27](=[O:28])[N:18]([CH2:17][CH2:16][CH2:15][CH2:14][N:11]3[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]4[CH:33]=[CH:34][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)[C:19](=[O:32])[NH:20]2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8030ThiopheneHCID 13851172HCID 13851172, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13851173HCID 13851173, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 30 parts of 3-[4-[4-(4-fluorobenzoyl)-1-piperidinyl]-butyl]-7-nitro-2,4(1H,3H)-quinazolinedione, 500 parts of acetic acid and 2 parts of a solution of thiophene in methanol 4% was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over diatomaceous earth and the filtrate was evaporated. The residue was stirred in 80 parts of 2-propanol, 300 parts of water and 100 parts of ammonium hydroxide. The aqueous phase was decanted and the residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 27 parts (96%) of 7-amino-3-[4-[4-(4-fluorobenzoyl)-1-piperidinyl]butyl]-2,4(1H,3H)-quinazolinedione; mp. 213.0° C. (8).

Workup

  1. filtrationthe catalyst was filtered off over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe aqueous phase was decanted
  4. customthe residue was crystallized from acetonitrile
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-e35f8aa3c17a46e198696a615732a82e
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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