Acetic Acid → HCID 9844234, compound

HRID 1974644Notes

Reaction equation

HRID 1974644 reaction equation
C([NH:8][C:9]1[C:17]2[N:16](C3CC3)[C:15]3=[CH:21][C:22](=[O:34])[N:23]([O:26]CC4C=CC=CC=4)[C:24](=[O:25])[N:14]3[C:13]=2[C:12]([F:35])=[C:11]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:10]=1[F:43])C1C=CC=CC=1.[C:44](O)(=O)[CH3:45].[CH2:48](O)C>[Pd]>[NH2:8][C:9]1[C:17]2[N:16]3[C:24](=[O:25])[N:23]([OH:26])[C:22](=[O:34])[CH:21]=[C:15]3[N:14]([CH:45]3[CH2:44][CH2:48]3)[C:13]=2[C:12]([F:35])=[C:11]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:10]=1[F:43]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 19101718HCID 19101718, compound

Product 1

HCID 9844234HCID 9844234, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

6-Benzylamino-2-benzyloxy-5-cyclopropyl-7,9-difluoro-8-(4-methylpiperazin-1-yl)-1,2,3,5-tetrahydro-pyrimido[1,6-a]benzimidazole-1,3-dione(0.57 g, 0.97 mmol), dissolved in ethanol (115 ml) and concentrated acetic acid (15 ml), is hydrogenated over 5% Pd/C (150 mg). At the end of the reaction, the catalyst is filtered off, and the solution is evaporated. The residue is dissolved in water (10 ml) and the pH adjusted to 7-8 with saturated aqueous sodium bicarbonate solution. The resulting crystals are collected by filtration, washed with water (10 ml) and dried, affording 0.32 g of 9-amino-5-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-2-hydroxy-pyrimido[1,6-a]benzimidazole-1,3-(2H, 5H)-dione as colorless crystals (80%): mp>250° C. (dec); NMR (DMSO-d6): 0.97 (m,2H), 1.14 (m,2H), 2.22 (s,3H), 2.43 (m,4H), 3.13 (m,5H), 5.30 (s,1H), 6.25 (s,2H), 10.80 (broad, 1H).

Workup

  1. customAt the end of the reaction
  2. filtrationthe catalyst is filtered off
  3. customthe solution is evaporated
  4. dissolutionThe residue is dissolved in water (10 ml)
  5. filtrationThe resulting crystals are collected by filtration
  6. washwashed with water (10 ml)
  7. customdried

Sources & evidence

ORD record
ord-840a455ea0494fecb8c0200df3936286
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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