Dichloromethane → HCID 22137863, compound

HRID 1836996Notes

Reaction equation

HRID 1836996 reaction equation
ClCCl.[Cl:4][C:5]1[CH:6]=[C:7]([N:11]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[C:12]([C:14]2[O:15][C:16]3[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]=2O)=[NH:13])[CH:8]=[CH:9][CH:10]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[Cl:4][C:5]1[CH:6]=[C:7]([N:11]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[C:12]([C:14]2[O:15][C:16]3[C:23]([NH:24][C:32](=[O:34])[CH3:33])=[CH:22][CH:21]=[CH:20][C:17]=3[CH:18]=2)=[NH:13])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 135830899HCID 135830899, compound

Product 1

HCID 22137863HCID 22137863, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a dichloromethane solution of 42 mg of N-(3-chloro-phenyl)-hydroxy-7-amino-N-(tetrahydro-pyran-2-yloxy)-benzofuran-2-carboxamidine was 200 μl of pyridine and 200 μl of acetic anhydride. The resulted solution was stirred at room temperature for 20 min. The reaction mixture was concentrated under vacuum. The crude product was purified by flash chromatography on silica gel eluted with 5-10% methanol/dichloromethane to give 43 mg of N-{2-[N-(3-chloro-phenyl)-N-(tetrahydro-pyran-2-yloxy)-carbamimidoyl]-benzofuran-7-yl}-acetamide in 99% yield.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe crude product was purified by flash chromatography on silica gel
  3. washeluted with 5-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-b518d6cf96344db88a3513d6afa64a6a
Source dataset
uspto-grants-2004_08
Patent number
US06780858B2

Reaction notes

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