Acetic Acid → HCID 22467465, compound

HRID 1934655Notes

Reaction equation

HRID 1934655 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[C:8]([CH:22]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1)=[O:10])([O-:3])=[O:2].[C:30](O)(=[O:32])[CH3:31].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[C:30]([N:27]1[CH2:28][CH2:29][CH:24]([NH:23][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:22][C:8]=2[C:9]([NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]3[O:17][CH2:18][O:19][C:15]=3[CH:14]=2)=[O:10])[CH2:25][CH2:26]1)(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22467525HCID 22467525, compound

Product 1

HCID 22467465HCID 22467465, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-nitro-2-(4-piperidinylamino)-N-(1,3-benzodioxol-5-ylmethyl)benzamide (80.0 mg), acetic acid (13.3 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (57.7 mg) and 1-hydroxybenzotriazole (40.7 mg) in anhydrous dimethylformamide (1 mL) was stirred for 3 hours at ambient temperature. The mixture was partitioned between water and ethyl acetate. The organic layer was separated and washed with an aqueous saturated sodium bicarbonate solution, water and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 2-(1-acetyl-4-piperidinylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (81.1 mg).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with an aqueous saturated sodium bicarbonate solution, water and brine
  4. dry with materialThen, the resultant was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-81bbad0f326e40f3b9d1136fe9f821e2
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

Loading…