Methanol → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-amino-1-aminomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

HRID 930158Notes

Reaction equation

HRID 930158 reaction equation
[N:1]([CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[N:20]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:21]=[C:22]([C:24]#[N:25])[N:23]=2)=[O:18])=[C:12]([C:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=2)[CH:11]=1)[CH2:6][N:7]=[N+]=[N-])=[N+]=[N-].O.CO.[NH4+].[Cl-]>C1COCC1.[Zn]>[NH2:7][CH2:6][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[N:20]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:31])[CH3:32])[CH:21]=[C:22]([C:24]#[N:25])[N:23]=2)=[O:18])=[C:12]([C:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=2)[CH:11]=1)[CH2:4][NH2:1]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 866158984-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-azido-1-azidomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

Product 1

HCID 597712334-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-amino-1-aminomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amideYield 42%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-azido-1-azidomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide (as prepared above, 546 mg, 1.00 mmol) was dissolved in THF (1 mL), water (2 mL) and MeOH (10 mL). To this solution NH4Cl (534 mg, 25.0 mmol) and Zn powder (653 mg, 10.0 mmol) were added with cooling. The resulting mixture was stirred at RT for 30 min and filtered through a thin pad of Celite. The filter cake was washed with MeOH (2×10 mL). The filtrate was concentrated, dissolved in 5% i-PrOH/DCM and washed with satd aq NaHCO3 (20 mL). The organic layer was dried (Na2SO4) and concentrated to obtain the title compound (207 mg, 42%): Mass spectrum (ESI, m/z): Calcd. for C26H38N6O2Si, 495.3 (M+H). found 495.2.

Workup

  1. temperaturewith cooling
  2. filtrationfiltered through a thin pad of Celite
  3. washThe filter cake was washed with MeOH (2×10 mL)
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in 5% i-PrOH/DCM
  6. washwashed with satd aq NaHCO3 (20 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-56070a778862491aab1ff530b81f43cd
Source dataset
uspto-grants-2016_03
Patent number
US09296726B2

Reaction notes

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