Diisopropylethylamine → HCID 86635093, compound

HRID 1696200Notes

Reaction equation

HRID 1696200 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].Cl.[CH3:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]1[NH2:20].[CH:21](N(CC)C(C)C)(C)C>CC(O)C>[CH3:21][N:20]([C@H:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]1[CH3:13])[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 40716944-Chloro-3-nitropyridin-2-amineHCID 67278079(1S,2R)-2-methylcyclohexanamine hydrochloride

Product 1

HCID 86635093HCID 86635093, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a microwave reaction vessel 4-chloro-3-nitro-2-pyridinamine (70 mg) and (1S,2R)-2-methylcyclohexanamine hydrochloride (66 mg) were suspended in 2-propanol (0.35 mL). To the mixture was added N,N-diisopropylethylamine (0.21 mL). The vessel was sealed and reacted in the microwave reactor at 130° C. for 1hour. 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-methyl-N4-[(1S,2R)-2-methylcyclohexyl]-3-nitro-2,4-pyridinediamine (75 mg) as a yellow amorphous.

Workup

  1. customThe vessel was sealed
  2. customreacted in the microwave reactor at 130° C. for 1hour
  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-a7947375685944a28bf6bb43aaa39647
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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