4-Methylmorpholine → HCID 18375839, compound

HRID 2268966Notes

Reaction equation

HRID 2268966 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:13][NH:14][O:15][CH3:16].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:13][N:14]([O:15][CH3:16])[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:1]=[CH:2][NH:3][C:4]=2[CH:9]=1)=[O:12]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 4594565-Benzimidazolecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18375839HCID 18375839, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-benzimidazolecarboxylic acid (1.62 g, 10 mmol) in CH2Cl2 (30 mL) was added N,O-dimethylhydroxylamine (1.17 g, 12 mmol), N-methylmorpholine (1.65 mL, 15 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.3 g, 12 mmol), respectively at room temperature. After stirring for 24 h, the reaction mixture was filtered to remove solid and rinsed thoroughly with CH2Cl2. The combined filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography using 5% MeOH/CH2Cl2 as an eluent to obtain 890 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.02 (s, 2H); 7.59 (d, J=7.6 Hz, 2H); 3.58 (s, 3H); 3.4 (s, 3H).

Workup

  1. customrespectively at room temperature
  2. filtrationthe reaction mixture was filtered
  3. customto remove solid
  4. washrinsed thoroughly with CH2Cl2
  5. concentrationThe combined filtrate was concentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-40848c134c984d58bf2d8c6d520864cc
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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