Tetrahydrofuran → HCID 12852074, compound

HRID 1248249Notes

Reaction equation

HRID 1248249 reaction equation
[NH2:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:5].[O:29]1CCC[CH2:30]1>>[F:28][C:26]1[CH:27]=[C:2]2[C:3]([C:4](=[O:5])[N:6]([CH2:7][CH2:8][N:9]3[CH2:14][CH2:13][CH:12]([C:15](=[O:23])[C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)[CH2:11][CH2:10]3)[C:30](=[O:29])[NH:1]2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 20278962HCID 20278962, compound

Product 1

HCID 12852074HCID 12852074, compoundYield 30%

Procedure

A mixture of 2.2 parts of 2-amino-4-fluoro-N-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]benzamide, 1.2 parts of 1,1'-bis[1H-imidazol-1-yl]methanone and 45 parts of tetrahydrofuran is stirred and refluxed for 3 hours. The reaction mixture is cooled and the solvent is evaporated. The residue is boiled in 4-methyl-2-pentanone. The solid product is filtered off and crystallized from N,N-dimethylformamide, yielding 0.8 parts (30%) of 7-fluoro-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione; mp. 248° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated
  4. filtrationThe solid product is filtered off
  5. customcrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-5a1dc2062d3448dd8c48ae4064c001a3
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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