Chloroform → 4-Oxo-4-(2-(5-(benzoxazol-2-yl)-2-methylbenzimidazol-1-yl)ethyl)aminobutyric acid

HRID 74290Notes

Reaction equation

HRID 74290 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:23].[C:24]1(=[O:30])[O:29][C:27](=[O:28])[CH2:26][CH2:25]1.C(N(CC)CC)C.C(Cl)(Cl)Cl>O>[O:30]=[C:24]([NH:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:23])[CH2:25][CH2:26][C:27]([OH:29])=[O:28]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 674977031-(2-Aminoethyl)-5-(benzoxazol-2-yl)-2-methylbenzimidazole hydrochloride

Product 1

HCID 674982864-Oxo-4-(2-(5-(benzoxazol-2-yl)-2-methylbenzimidazol-1-yl)ethyl)aminobutyric acidYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Aminoethyl)-5-(benzoxazol-2-yl)-2-methylbenzimidazole hydrochloride (see Working Example 56) (0.20 g, 0.6 mmol), succinic anhydride (0.06 g, 0.6 mmol), triethylamine (0.22 g, 2.2 mmol) and CHCl3 (2 mL) were added together, and after stirring for 1 hour at room temperature this was heated to reflux with stirring for 1 hour. After cooling, water was added and back-extraction was carried out. The aqueous layer obtained was concentrated, and the residue was reslurried in methanol. After the precipitated crystals were filtered, they were dried to yield the title compound (0.13 g, 69% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. stirringwith stirring for 1 hour
  4. temperatureAfter cooling
  5. extractionback-extraction
  6. customThe aqueous layer obtained
  7. concentrationwas concentrated
  8. filtrationAfter the precipitated crystals were filtered
  9. customthey were dried

Sources & evidence

ORD record
ord-ee821764ec77435eb0092ee1bdeb1763
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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