Hydrogen Bromide → HCID 19101723, compound

HRID 1974634Notes

Reaction equation

HRID 1974634 reaction equation
[CH2:1]([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(OC(C)(C)C)=O)[CH2:22][CH2:21]4)[C:17]([F:33])=[CH:16][C:15]=3[N:11]2[C:10]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br>C(O)(=O)C>[CH2:1]([O:8][N:9]1[C:38](=[O:39])[CH:37]=[C:12]2[N:13]([CH:34]3[CH2:35][CH2:36]3)[C:14]3[CH:19]=[C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:17]([F:33])=[CH:16][C:15]=3[N:11]2[C:10]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 15751520HCID 15751520, compound

Product 1

HCID 19101723HCID 19101723, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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 (580 mg, 1.05 mmol) is treated with 33 percent hydrobromic acid in glacial acetic acid (5 ml). After 18 hours at room temperature the separated crystals are filtered off, washed with glacial acetic acid and recrystallized from methanol. The crystals are then dissolved in a water/ethanol mixture (2:1, 50 ml). The pH is adjusted to 8 using 1N sodium hydroxide solution, whereby white crystals separate. The crystals are filtered off, washed with water and dried in a high vacuum. There are obtained 417 mg (88%) of 2-(benzyloxy)-5-cyclopropyl-8-fluoro-7-(1-piperazinyl)pyrimido[1,6-a]benzimidazole-1,3(2H,5H)-dione.

Workup

  1. filtrationAfter 18 hours at room temperature the separated crystals are filtered off
  2. washwashed with glacial acetic acid
  3. customrecrystallized from methanol
  4. dissolutionThe crystals are then dissolved in a water/ethanol mixture (2:1, 50 ml)
  5. customseparate
  6. filtrationThe crystals are filtered off
  7. washwashed with water
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-b4447a9c46e84aa1926fb730c6ecc93e
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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