Benzaldehyde → HCID 44218795, compound

HRID 452551Notes

Reaction equation

HRID 452551 reaction equation
[O:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:21]2[N:22]=[C:23]([NH2:26])[NH:24][CH:25]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)[CH3:2].[CH:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C1COCC1>[NH2:26][C:23]1[NH:24][C:25]([CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[OH:34])=[C:21]([C@H:9]([C:6]2[CH:7]=[CH:8][C:3]([O:1][CH3:2])=[CH:4][CH:5]=2)[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=2)[N:22]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 10340Sodium CarbonateHCID 178490615HCID 178490615, compound

Product 1

HCID 44218795HCID 44218795, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{(1S)-1-(4-methoxylphenyl)-2-[4-(trifluoromethyl)phenyl]ethyl}-1H-imidazole-2-amine (0.05 g, 0.14 mmol) in H2O (1 mL) and THF (0.5 mL) was added benzaldehyde (0.018 g, 0.17 mmol) and sodium carbonate (0.01 g, 0.08 mmol). The reaction was stirred at room temperature for 12 h. The reaction was concentrated and purified by RP HPLC to provide (2-amino-4-{(1S)-1-(4-methoxyphenyl)-2-[4-(trifluoromethyl)phenyl]ethyl}-1H-imidazole-5-yl) (phenyl)methanol (0.01 g, 14%).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by RP HPLC

Sources & evidence

ORD record
ord-21807cd34e8f422d9e787d288fe9380a
Source dataset
uspto-grants-2013_07
Patent number
US08492387B2

Reaction notes

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