Triethylamine → HCID 19101710, compound

HRID 1974637Notes

Reaction equation

HRID 1974637 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([F:40])=[CH:16][C:17]3[N:21]=[C:20]([CH2:22][C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=4)=[O:24])[N:19]([CH:36]4[CH2:38][CH2:37]4)[C:18]=3[CH:39]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC[C:50]([N:52]=[C:53]=[O:54])=[O:51]>C1COCC1>[CH:36]1([N:19]2[C:18]3[CH:39]=[C:14]([N:11]4[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]4)[C:15]([F:40])=[CH:16][C:17]=3[N:21]3[C:50](=[O:51])[NH:52][C:53](=[O:54])[CH:22]([C:23]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=4)=[O:24])[CH:20]23)[CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78209Chloroacetyl isocyanateHCID 19101726HCID 19101726, compound

Product 1

HCID 19101710HCID 19101710, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-nitrobenzyl 6-[4-(tert-butoxycarbonyl)-1-piperazinyl]-1-cyclopropyl-5-fluoro-2-benzimidazole acetate (553 mg, 1 mmol) in THF (50 ml) is treated in succession at 0° with triethylamine (300 mg, 3 mmol) and chloroacetyl isocyanate (298 mg, 2.5 mmol). After stirring for 20 hours the solvent is distilled off and the residues is taken up in ethyl acetate and washed in succession with water (50 ml) and 10 percent sodium chloride solution (50 ml). The organic phase is dried over magnesium sulfate and the solvent is evaporated. The residue is recrystallized from ethyl acetate. There are obtained 373 mg (59%) of p-nitrobenzyl 5-cyclopropyl-8-fluoro-1,2,3,4-tetrahydro-1,3-dioxo-7-[4-(tert-butoxycarbonyl)-1-piperazinyl]pyrimido[1,6-a]benzimidazole-4-carboxylate.

Workup

  1. distillationis distilled off
  2. washwashed in succession with water (50 ml) and 10 percent sodium chloride solution (50 ml)
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is evaporated
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c2869670cc5a4392b1814a46a1ce69e3
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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