Acetic Anhydride → HCID 10089428, compound

HRID 2243820Notes

Reaction equation

HRID 2243820 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[N:8]12[CH2:16][CH2:15][CH:12]([CH2:13][CH2:14]1)[N:11]([C:17]([C:19]1[O:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=3)=[CH:22][CH:23]=1)=[O:18])[CH2:10][CH2:9]2.[OH-].[Na+]>ClCCl>[N:8]12[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16]1)[N:11]([C:17]([C:19]1[O:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:1](=[O:3])[CH3:2])=[CH:26][CH:25]=3)=[CH:22][CH:23]=1)=[O:18])[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 10425586HCID 10425586, compound

Product 1

HCID 10089428HCID 10089428, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetic acid anhydride (133 mg; 1.3 mmol) solved in dichloromethane (2 ml) was added dropwise to a mixture of (1,4-diaza-bicyclo[3.2.2]non-4-yl)-5-(4-aminophenyl)-furan-2-yl-methanone and dichloromethane (10 ml) at room temperature. The mixture was allowed to stir for 4 hours. Aqueous sodium hydroxide (20 ml; 1M) was added followed by extraction with dichloromethane (3×20 ml). The crude mixture was purified by silica gel chromatography, using a mixture of dichloromethane:methanol (4:1) and 2% methanol as eluent. The product was isolated as the free base. Mp. 113° C. (decomp.).

Workup

  1. extractionfollowed by extraction with dichloromethane (3×20 ml)
  2. customThe crude mixture was purified by silica gel chromatography
  3. additiona mixture of dichloromethane:methanol (4:1) and 2% methanol as eluent
  4. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-b121725932e94f2c9a97a63496099174
Source dataset
uspto-grants-2010_03
Patent number
US07678788B2

Reaction notes

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