Tetrahydrofuran → 2-(4-tert-Butyl-3-chlorophenoxy)-N-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]acetamide

HRID 2108833Notes

Reaction equation

HRID 2108833 reaction equation
C1COCC1.[C:6]([C:10]1[CH:20]=[CH:19][C:13]([O:14][CH2:15][C:16]([OH:18])=O)=[CH:12][C:11]=1[Cl:21])([CH3:9])([CH3:8])[CH3:7].C1N=CN(C(N2C=NC=C2)=O)C=1.C(C1C=CC(OCC([NH:46][CH2:47][C:48]2[CH:57]=[CH:56][C:51]3[NH:52][C:53](=[O:55])[NH:54][C:50]=3[CH:49]=2)=O)=CC=1)(C)(C)C>C(N(CC)CC)C>[C:6]([C:10]1[CH:20]=[CH:19][C:13]([O:14][CH2:15][C:16]([NH:46][CH2:47][C:48]2[CH:57]=[CH:56][C:51]3[NH:52][C:53](=[O:55])[NH:54][C:50]=3[CH:49]=2)=[O:18])=[CH:12][C:11]=1[Cl:21])([CH3:7])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 159797742-(4-Tert-butylphenoxy)-n-[(2-oxo-2,3-dihydro-1h-benzimidazol-5-yl)methyl]acetamideHCID 21097497(4-tert-Butyl-3-chlorophenoxy)acetic acid

Product 1

HCID 159797772-(4-tert-Butyl-3-chlorophenoxy)-N-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]acetamideYield 11%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a THF (3.0 ml) solution of the compound of 4A (109 mg, 0.45 mmol) was added CDI (73 mg, 0.45 mmol) at room temperature and the mixture was stirred for 2 hours followed by the additional stirring for 10 hours after the injection of triethylamine (0.3 ml) and the amine compound of Example 1 (156 mg, 0.5 mmol). The resulting precipitate was removed by filtration, followed by evaporation under reduced pressure to give the crude residue which was purified through silica gel column chromatography eluting with DCM/MeOH (9:1) to furnish the title compound as a white solid (19 mg, 11%). 1H NMR (CDCl3): δ 1.40 (9H, s), 4.29 (2H, d, J=5.9 Hz), 4.53 (2H, s), 6.78-6.92 (4H, m), 7.01 (1H, d, J=2.6 Hz), 7.37 (1H, d, J=8.5 Hz), 8.61 (1H, bt, J=6.6 Hz), 10.55, 1H, bs), 10.57 (1H, bs). MS (ESI) m/z 388 (M+H)+.

Workup

  1. customThe resulting precipitate was removed by filtration
  2. customfollowed by evaporation under reduced pressure
  3. customto give the crude residue which
  4. customwas purified through silica gel column chromatography
  5. washeluting with DCM/MeOH (9:1)

Sources & evidence

ORD record
ord-bb625c18640a4b7eb11a684059e04731
Source dataset
uspto-grants-2009_04
Patent number
US07514457B2

Reaction notes

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