Hydrochloric Acid → 3-(1-(4-(1H-benzo[d]imidazol-1-yl)pyrimidin-2-ylamino)ethyl)-4-benzyl-N-(naphthalen-1-yl)piperazine-1-carboxamide

HRID 429289Notes

Reaction equation

HRID 429289 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH:14]([NH:16][C:17]2[N:22]=[C:21]([N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]=[CH:24]3)[CH:20]=[CH:19][N:18]=2)[CH3:15])[CH2:9]1)=O)(C)(C)C.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([O-])([O-])=O.[K+].[K+].Cl.CCO[C:50]([CH3:52])=O>CN(C=O)C>[CH2:32]([N:11]1[CH2:12][CH2:13][N:8]([C:6](=[O:5])[NH:8][C:9]2[C:50]3[C:52](=[CH:31][CH:26]=[CH:27][CH:28]=3)[CH:15]=[CH:14][CH:10]=2)[CH2:9][CH:10]1[CH:14]([NH:16][C:17]1[N:22]=[C:21]([N:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:25]=[CH:24]2)[CH:20]=[CH:19][N:18]=1)[CH3:15])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 702154342-[1-(4-(Tert-butyloxycarbonyl)-piperazine-2-yl)-ethylamino]-4-(benzimidazol-1-yl)-pyrimidine

Product 1

HCID 207036243-(1-(4-(1H-benzo[d]imidazol-1-yl)pyrimidin-2-ylamino)ethyl)-4-benzyl-N-(naphthalen-1-yl)piperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[1-(4-(tert-butyloxycarbonyl)-piperazine-2-yl)-ethylamino]-4-(benzimidazol-1-yl)-pyrimidine (2 mg) in 0.5 mL of DMF was added benzyl bromide (1.1 μL) and K2CO3 (1.3 mg). The mixture was stirred overnight at room temperature, then diluted with 5 mL of EtOAc and poured into 10 mL of 1N HCl. The phases were separated and the aqueous phase was basified (pH>11) with 5N NaOH and extracted with 4×5 mL of EtOAc. The combined organics were dried over Na2SO4 and concentrated. The residue was dissolved in 0.5 mL of CH2Cl2 and 0.25 mL of trifluoroacetic acid was added. The mixture was stirred for 2 h at room temperature, then concentrated. The residue was dissolved in 0.5 mL of pyridine and naphthyl isocyanate (1 μL) was added. The mixture was stirred overnight at room temperature, then co-concentrated with heptane. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2—MeOH to provide 0.9 mg of the title compound. Mass spectrum (ESI) 583.5 (M+1).

Workup

  1. customThe phases were separated
  2. extractionextracted with 4×5 mL of EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 0.5 mL of CH2Cl2
  6. addition0.25 mL of trifluoroacetic acid was added
  7. stirringThe mixture was stirred for 2 h at room temperature
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in 0.5 mL of pyridine
  10. additionnaphthyl isocyanate (1 μL) was added
  11. stirringThe mixture was stirred overnight at room temperature
  12. customThe residue was purified by preparative thin-layer chromatography
  13. washeluting with 95:5 CH2Cl2—MeOH

Sources & evidence

ORD record
ord-38b3a5247f1648359366002efb18ef56
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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