Diisopropylethylamine → N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-3-nitro-2,4-pyridinediamine

HRID 1696198Notes

Reaction equation

HRID 1696198 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([N:19]1[CH2:24][CH2:23][C@@H:22]([CH3:25])[C@@H:21]([NH:26][CH3:27])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C>CC(O)C>[CH2:12]([N:19]1[CH2:24][CH2:23][C@@H:22]([CH3:25])[C@@H:21]([N:26]([CH3:27])[C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=2[N+:9]([O-:11])=[O:10])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 40716944-Chloro-3-nitropyridin-2-amineHCID 44630604(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine

Product 1

HCID 86635092N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-3-nitro-2,4-pyridinediamineYield 89.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a microwave reaction vessel 4-chloro-3-nitro-2-pyridinamine (125 mg) and (3R,4R)-1-benzyl-N,4-dimethyl-3-piperidinamine (314 mg) were suspended in 2-propanol (6.25 mL). To the mixture was added N,N-diisopropylethylamine (0.63 mL). The vessel was sealed and reacted in the microwave reactor at 135° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-3-nitro-2,4-pyridinediamine (230 mg) as a yellow amorphous.

Workup

  1. customThe vessel was sealed
  2. customreacted in the microwave reactor at 135° C. for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

Sources & evidence

ORD record
ord-13c14b96a028451498f3219f8b065cbe
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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