4-Methylbenzaldehyde → HCID 178425443, compound

HRID 1297186Notes

Reaction equation

HRID 1297186 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=3[N:17]=2)=[CH:12][CH:11]=1.[C:28]1([CH3:36])[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN(C=O)C>[CH3:36][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=4[N:17]=3)=[CH:14][CH:15]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 178513585HCID 178513585, compound

Product 1

HCID 178425443HCID 178425443, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(2-piperidin-2-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide (0.10 g, 0.27 mmol) in DMF (1 mL) was added p-tolualdehyde (70 μL, 0.59 mmol), activated 4 Å molecular sieves, and NaB(OAc)3H (0.175 g, 0.82 mmol). The solution was stirred for 16 h and additional portions of aldehyde (1 equiv.) and NaB(OAc)3H (3 equiv.) were added. When HPLC monitoring indicated reaction completion, the solution was quenched with 1 N NaOH and purified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA), providing 60 mg (48%) of product. HPLC (Method C): Rt=4.60. MS (ESI+): mass calcd. for C29H32N4O2, 468.25; m/z found, 469.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.18 (s, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.94 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.34-7.32 (m, 2H), 7.23-7.20 (m, 2H), 7.15-7.13 (m, 2H), 4.33-4.10 (m, 3H), 3.45-3.39 (m, 1H), 3.15-3.07 (m, 1H), 2.90-2.85 (m, 1H), 2.72-2.67 (m, 1H), 2.42-2.37 (m, 1H), 2.20-2.10 (m, 1H), 1.93 (br s, 1H), 1.88-1.73 (m, 2H), 1.73-1.45(m, 3H).

Workup

  1. customreaction completion
  2. customthe solution was quenched with 1 N NaOH
  3. custompurified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA)

Sources & evidence

ORD record
ord-9e8bbbc68b334afca44d6e84a49d298a
Source dataset
uspto-grants-2007_07
Patent number
US07250427B2

Reaction notes

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