HCID 15751522, compound → HCID 19101719, compound

HRID 1974639Notes

Reaction equation

HRID 1974639 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:39]([F:40])=[CH:38][C:17]3[N:18]4[C:27](=[O:28])[N:26]([NH:29]C(OC(C)(C)C)=O)[C:25](=[O:37])[CH:24]=[C:19]4[N:20]([CH:21]4[CH2:23][CH2:22]4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:29][N:26]1[C:25](=[O:37])[CH:24]=[C:19]2[N:20]([CH:21]3[CH2:23][CH2:22]3)[C:16]3[CH:15]=[C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[C:39]([F:40])=[CH:38][C:17]=3[N:18]2[C:27]1=[O:28]

Participants

3

Reactant 1

HCID 15751522HCID 15751522, compound

Product 1

HCID 19101719HCID 19101719, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 7-[4-(tert-butoxycarbonyl)-1-piperazinyl]-5-cyclopropyl-8-fluoro-3,5-dihydro-1,3-dioxopyrimido-[1,6-a]benzimidazol-2(1H)-carbamate (0.145 g, 0.26 mmol) is dissolved in 1 ml of trifluoroacetic acid and stirred at room temperature for 2 hours. The reaction solution is concentrated, treated with 1 ml of H2O, adjusted to pH 8 with saturated aqueous NaHCO3 solution and stirred at room temperature for 1 hour. The suspension is cooled to 0° and suction filtered. The product is chromatographed on silica gel (eluent: CHCl3 /EtOH/NH4OH 80:20:1) and recrystallized from ethanol. There is obtained 2-amino-5-cyclopropyl-8-fluoro-7-(1-piperazinyl)pyrimido[1,6-a]benzimidazole-1,3(2H,5H)-dione. Yield: 43 mg (46%); m.p. 232°-234°.

Workup

  1. concentrationThe reaction solution is concentrated
  2. additiontreated with 1 ml of H2O
  3. stirringstirred at room temperature for 1 hour
  4. temperatureThe suspension is cooled to 0°
  5. filtrationsuction filtered
  6. customThe product is chromatographed on silica gel (eluent: CHCl3 /EtOH/NH4OH 80:20:1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-bf5e4413a3dc424e9000aad8fb30f27e
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

Loading…