1-Methyl-2-imidazolecarboxaldehyde → HCID 58996678, compound

HRID 1592756Notes

Reaction equation

HRID 1592756 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[CH3:21][N:22]1[CH:26]=[CH:25][N:24]=[C:23]1[CH:27]=O.[BH4-].[Na+]>CO>[CH3:21][N:22]1[CH:26]=[CH:25][N:24]=[C:23]1[CH2:27][NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 58996678HCID 58996678, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-boc-4-(2-aminophenyl) piperazine (554 mg, 2.0 mmol, 1.0 eq.) in methanol was added (1-methyl-1H-imidazole-2-carbaldehyde (220 mg, 2.0 mmol, 1.0 eq.). The mixture was reflux for about 1 hour and then cool to about 0° C. Sodium borohydride on alumina (10 wt % on basic alumina, 1.13 g, 3.0 mmol, 1.5 eq.) was added. The solution was warmed to r.t. and then stirred overnight. The reaction mixture was filtered through celite and then concentrated. Purification by flash chromatography (35 g SiO2, 40 mL/min, linear gradient, 0-8% MeOH/CH2Cl2 for 25 minutes and then 8% MeOH for 7 minutes) afforded Boc protected title compound (176 mg, 0.47 mmol, 24%). LRMS (ESI+): 372.3 [M+1].

Workup

  1. temperatureThe mixture was reflux for about 1 hour
  2. temperatureThe solution was warmed to r.t.
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationconcentrated
  5. customPurification by flash chromatography (35 g SiO2, 40 mL/min, linear gradient, 0-8% MeOH/CH2Cl2 for 25 minutes
  6. custom8% MeOH for 7 minutes) afforded Boc

Sources & evidence

ORD record
ord-24dca1db2bcb4217b5299b11bba55a22
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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