Ethylenediamine → HCID 178435785, compound

HRID 2174004Notes

Reaction equation

HRID 2174004 reaction equation
[CH2:1]([C:3]1[C:4]([C:23]([C:26]2[N:30](COCC[Si](C)(C)C)[C:29]3[CH:39]=[CH:40][C:41]([C:43]#[N:44])=[CH:42][C:28]=3[N:27]=2)([OH:25])[CH3:24])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:7]=[CH:6]2)[CH3:2].C(C1C(C(C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)(O)C)=C2C(=C(C)C=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2)C.C(N)CN.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>>[CH2:1]([C:3]1[C:4]([C:23]([C:26]2[NH:30][C:29]3[CH:39]=[CH:40][C:41]([C:43]#[N:44])=[CH:42][C:28]=3[N:27]=2)([OH:25])[CH3:24])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=1)(=[O:15])=[O:14])[CH:7]=[CH:6]2)[CH3:2]

Participants

6

Reactant 5

HCID 3301EthylenediamineHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86701583HCID 86701583, compoundHCID 86701584HCID 86701584, compound

Product 1

HCID 178435785HCID 178435785, compound

Conditions

Temperature
60 °C

Procedure

To a solution of a mixture of (±)-2-(1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)-1-hydroxyethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-(1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)-1-hydroxyethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (1.5 g, 2.38 mmol) and ethylenediamine (1.61 mL, 23.85 mmol) was added TBAF in THF (1M, 23.85 mL, 23.85 mmol), and then the mixture was stirred at 60° C. for 3 h. The reaction was quenched by H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The organic phase was successively washed with H2O and brine, dried over Na2SO4, and filtered. After concentration of the filtrate the resulting residue was purified by silica gel flash chromatography (heptanes/EtOAc=66/34, isocratic) to give the title compound. MS (ESI+) m/z 499.3 (M+H).

Workup

  1. customThe reaction was quenched by H2O
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe organic phase was successively washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customAfter concentration of the filtrate the resulting residue was purified by silica gel flash chromatography (heptanes/EtOAc=66/34, isocratic)

Sources & evidence

ORD record
ord-85da976368804f19a6b3a0c3c3798085
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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