Diisopropylethylamine → 1-(4-{[4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-2-phenylethane-1,2-dione

HRID 1354802Notes

Reaction equation

HRID 1354802 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:18])[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[NH:27][C:26]2=[O:34])[CH2:21][CH2:20]1.CCN(C(C)C)C(C)C>C1COCC1.CO>[O:34]=[C:26]1[N:25]([CH:22]2[CH2:21][CH2:20][N:19]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([C:9](=[O:18])[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[O:11])=[CH:5][CH:4]=3)[CH2:24][CH2:23]2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[NH:27]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 875021-[4-(Bromomethyl)phenyl]-2-phenylethane-1,2-dioneHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Product 1

HCID 211031941-(4-{[4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-2-phenylethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 1-[4-(bromomethyl)phenyl]-2-phenylethane-1,2-dione (6.06 g, 20.0 mmol), 1-piperidin-4-yl-1,3-dihydro-2H-benzimidazol-2-one (4.56 g, 21.0 mmol), PS-DIEA (20 g, 74 mmol), and TEA (50 mg, 0.5 mmol) was stirred overnight at rt in THF-MeOH (1:1, 300 mL). After this time, the resin (PS-DIEA) was filtered and washed with MeOH (2×100 mL). The combined solution was concentrated to afford the desired product. This product is pure enough (by LCMS) for next step reaction. Analytical LCMS: single peak (ELSD), 2.483 min.

Workup

  1. filtrationAfter this time, the resin (PS-DIEA) was filtered
  2. washwashed with MeOH (2×100 mL)
  3. concentrationThe combined solution was concentrated

Sources & evidence

ORD record
ord-a7306a4ad9db48f4bbdde66fc493ef90
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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