Dimethylamine → HCID 178484630, compound

HRID 1433212Notes

Reaction equation

HRID 1433212 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:32]=[CH:31][C:15]2[NH:16][C:17]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:14]=2[CH:13]=1)[C:3]([OH:5])=O.[CH:33]([N:36](C(C)C)[CH2:37]C)(C)C.CNC>CN(C=O)C>[CH3:33][N:36]([CH3:37])[C:3](=[O:5])[CH:2]([OH:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:32]=[CH:31][C:15]2[NH:16][C:17]([CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=3)=[N:18][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 178525951HCID 178525951, compound

Product 1

HCID 178484630HCID 178484630, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of hydroxy-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-acetic acid (0.030 g, 0.0678 mmol) in DMF (0.5 mL) was added (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) (0.033 g, 0.0745 mmol), diisopropylethylamine (DIPEA) (0.05 mL, 0.272 mmol), and dimethylamine (0.05 mL, 0.102 mmol, 2.0M solution in THF). After stirring for 12 hours, the crude product was purified by chromatography (silica, CH2Cl2: MeOH, 5:1) to afford the title compound as a white solid (0.028 g, 83%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.71-7.67 (m, 2H), 7.63 (d, 2H, J=8.4 Hz), 7.41-7.37 (m, 5H), 7.25 (d, 2H, J=8.8 Hz), 5.46 (s, 2H), 5.24 (s, 1H), 2.85 (s, 3H), 2.36 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H23F3N3O3: 470.5 (M+H), Found 470.3.

Workup

  1. customthe crude product was purified by chromatography (silica, CH2Cl2: MeOH, 5:1)

Sources & evidence

ORD record
ord-d832f1a777d4482cba8c775767e3342d
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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