Diisopropylethylamine → HCID 59704915, compound

HRID 605870Notes

Reaction equation

HRID 605870 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[CH:17][N:16]([C:19]3[N:24]=[C:23](SC#N)[C:22]([N+:28]([O-:30])=[O:29])=[CH:21][N:20]=3)[C:15]=2[CH:31]=1.Cl.[C:33]([O:37][C:38](=[O:42])[C@@H:39]([CH3:41])[NH2:40])([CH3:36])([CH3:35])[CH3:34]>C1COCC1>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[CH:17][N:16]([C:19]3[N:24]=[C:23]([NH:40][C@H:39]([CH3:41])[C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:42])[C:22]([N+:28]([O-:30])=[O:29])=[CH:21][N:20]=3)[C:15]=2[CH:31]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 16211919D-Alanine tert-butyl ester hydrochlorideHCID 59704880HCID 59704880, compound

Product 1

HCID 59704915HCID 59704915, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (2.6 mL) was added to a mixture of 6-chloro-1-(5-nitro-4-thiocyanatopyrimidin-2-yl)-1H-benzo[d]imidazole (1.66 g, 5 mmol) and D-alanine t-butyl ester hydrochloride (1.1 g, Chem-Impex Int.) in THF (50 mL). The combined mixture was stirred at RT overnight, partitioned between ethyl acetate and water then separated. The aqueous layer was extracted once again with ethyl acetate and the combined organics were concentrated and purified by column chromatography. Elution with DCM and 0.5% MeOH in DCM provided the above compound (0.58 g), MH+=419, 421.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customthen separated
  3. extractionThe aqueous layer was extracted once again with ethyl acetate
  4. concentrationthe combined organics were concentrated
  5. custompurified by column chromatography
  6. washElution with DCM and 0.5% MeOH in DCM

Sources & evidence

ORD record
ord-7fb3856d820f492db590bb0c1104495d
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

Loading…