Sodium Carbonate → 2-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-(2-tert.butyloxycarbonyl-azetidin-1-yl)-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

HRID 1067475Notes

Reaction equation

HRID 1067475 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([NH2:30])([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])[CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH:32]([CH2:40][CH2:41]Br)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([N:30]4[CH2:41][CH2:40][CH:32]4[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])[CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5107723tert-Butyl 2,4-dibromobutyrateHCID 181881512-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-amino-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

Product 1

HCID 700832612-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-(2-tert.butyloxycarbonyl-azetidin-1-yl)-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

0.8 g (1.86 mmol) of 2-(4-cyanophenylaminomethyl)-1-methyl-5-[1-amino-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole and 1.65 g ((5.5 mmol) of tert.butyl 2,4-dibromobutyrate are dissolved in 5 ml of ethanol, mixed with 0.2 g (1.86 mmol) of sodium carbonate and stirred under nitrogen for 30 hours at 55° C. After cooling, the white precipitate is filtered off and washed with ethanol. The filtrate is concentrated by evaporation, the residue is chromatographed on silica gel, eluting with ethyl acetate and ethyl acetate/ethanol/ammonia (20:1:0.01). The desired fractions are combined and concentrated by evaporation.

Workup

  1. temperatureAfter cooling
  2. filtrationthe white precipitate is filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate is concentrated by evaporation
  5. customthe residue is chromatographed on silica gel
  6. washeluting with ethyl acetate and ethyl acetate/ethanol/ammonia (20:1:0.01)
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-cdde9183850f4850b2f6a85ea4b02431
Source dataset
uspto-grants-2001_06
Patent number
US06248770B1

Reaction notes

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