Acetic Anhydride → HCID 86594879, compound

HRID 1354752Notes

Reaction equation

HRID 1354752 reaction equation
[CH3:1][N:2]([CH3:34])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=4[N+:31]([O-])=O)[CH2:20][CH2:19]3)=[O:17])=[CH:10][CH:9]=2)[CH2:4]1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>[Pd].C(O)(=O)C>[CH3:1][N:2]([CH3:34])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=4[NH:31][C:35](=[O:37])[CH3:36])[CH2:20][CH2:19]3)=[O:17])=[CH:10][CH:9]=2)[CH2:4]1

Participants

5

Reactant 2

HCID 7918Acetic Anhydride2×HCID 86594880HCID 86594880, compound

Product 1

HCID 86594879HCID 86594879, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Palladium on carbon (10%; 10 mg) was added to a solution of 1-(4-chloro-2-nitro-phenyl)piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]methylamide (50 mg) in glacial acetic acid (5 ml). The solution was stirred under a hydrogen atmosphere (1 bar), and acetic anhydride (14 μl) was added. After one hour, further acetic anhydride (6 μl) were added and the mixture was stirred for 15 minutes. The suspension was filtered and the filtrate was concentrated. The residue was purified by chromatography (silica gel, eluent: ethyl acetate/ammonia (7N in methanol)). This resulted in the product with the molecular weight of 498.07 (C27H36ClN5O2); MS (ESI): 498 (M+H+).

Workup

  1. additionwas added
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography (silica gel, eluent: ethyl acetate/ammonia (7N in methanol))
  5. customThis resulted in the product with the molecular weight of 498.07 (C27H36ClN5O2)

Sources & evidence

ORD record
ord-e166c8e293c94ff1b91188f79fef08f8
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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