HCID 15751520, compound → HCID 15751521, compound

HRID 1974631Notes

Reaction equation

HRID 1974631 reaction equation
C([O:8][N:9]1[C:38](=[O:39])[CH:37]=[C:12]2[N:13]([CH:34]3[CH2:36][CH2:35]3)[C:14]3[CH:19]=[C:18]([N:20]4[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]4)[C:17]([F:33])=[CH:16][C:15]=3[N:11]2[C:10]1=[O:40])C1C=CC=CC=1>C(O)C.[Pd]>[CH:34]1([N:13]2[C:14]3[CH:19]=[C:18]([N:20]4[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]4)[C:17]([F:33])=[CH:16][C:15]=3[N:11]3[C:10](=[O:40])[N:9]([OH:8])[C:38](=[O:39])[CH:37]=[C:12]23)[CH2:35][CH2:36]1

Participants

4

Reactant 1

HCID 15751520HCID 15751520, compound

Product 1

HCID 15751521HCID 15751521, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 4-[2-(benzyloxy)-5-cyclopropyl-8-fluoro-1,2,3,5-tetrahydro-1,3-dioxopyrimido[1,6-a]benzimidazol-7-yl]-1-piperazinecarboxylate (981 mg, 1.87 mmol) is dissolved in ethanol (250 ml) and hydrogenated with 5 percent palladium/carbon (200 mg) under hydrogen at normal pressure. The palladium/carbon is filtered off and washed with dimethylformamide (100 ml) at 100°. The combined filtrates are evaporated under reduced pressure. The residue is recrystallized from dimethylformamide. There are obtained 619 mg (72%) of tert-butyl 4-[5-cyclopropyl-8-fluoro-1,2,3,5-tetrahydro-2-hydroxy-1,3-dioxopyrimido[1,6-a]benzimidazol-7-yl]-1-piperazinecarboxylate.

Workup

  1. filtrationThe palladium/carbon is filtered off
  2. washwashed with dimethylformamide (100 ml) at 100°
  3. customThe combined filtrates are evaporated under reduced pressure
  4. customThe residue is recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-f63270a1bff14769bd74ed3e507195ef
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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