Acetic Acid → HCID 178470386, compound

HRID 536105Notes

Reaction equation

HRID 536105 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[NH2:11])=[O:5])[CH3:2].[BH3-]C#N.[Na+].CC(O)=O.[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[NH:25][C:26]([CH:28]=O)=[N:27][C:23]=2[CH:22]=1.[OH-].[Na+]>CO.C(OCC)(=O)C.CN(C=O)C.C(Cl)Cl>[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[NH:25][C:26]([CH2:28][NH:11][C:10]3[CH:9]=[CH:8][NH:7][C:6]=3[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:27][C:23]=2[CH:22]=1

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydride2×HCID 178519931HCID 178519931, compound2×

Product 1

HCID 178470386HCID 178470386, compoundYield 46.4%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of 3-amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.077 g, 0.5 mmol), NaCNBH3 (0.057 g, 0.9 mmol) and HOAc (0.030 g, 0.5 mmol) in methanol (4 mL) were stirred at r.t. fo 5 minutes before 5-chloro-1H-benzimidazole-2-carbaldehyde (0.144 g, 0.8 mmol) was added, followed by addition of CH2Cl2 (1 mL) and DMF (0.4 mL). The resulting mixture was allowed to stir for 16 h at r.t. under nitrogen atmosphere. Additional 5-chloro-1H-benzimidazole-2-carbaldehyde (0.030 g) and NaCNBH3 (0.015 g) were added and the reaction mixture was stirred at 4 h. The reaction mixture was neutralized with 2M NaOH and diluted with ethyl acetate. Extracted with water and the organic layer was dried (Na2SO4) and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate), obtaining 0.074 g (46%) of the title product.

Workup

  1. additionwas added
  2. stirringto stir for 16 h at r.t. under nitrogen atmosphere
  3. stirringthe reaction mixture was stirred at 4 h
  4. extractionExtracted with water
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-b3776406844e48698c248fd0815e09ec
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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