Dimethylacetamide → Ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylate

HRID 31939

Reaction equation

HRID 31939 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.[NH2:19][CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1.CCN(C(C)C)C(C)C.CC(N(C)C)=O>CCOC(C)=O>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([NH:22][CH2:21][CH2:20][NH:19][C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:3]=2)=[N:24][CH:25]=1)([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 1224252-(2-Aminoethylamino)-5-nitropyridineHCID 22142763Ethyl 6-chloro-4-phenylpyridine-3-carboxylate

Product 1

HCID 22143004Ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The crude material above, ethyl 6-chloro-4-phenylpyridine-3-carboxylate (140 mg, 0.56 mmol) was mixed with (2-aminoethyl)(5-nitro(2-pyridyl))amine (408 mg, 2.24 mmol), Hünig's base (390 ul), and DMA (2 ml) for 48 hours at 70-75° C. with stirring under argon. The reaction was followed by TLC and HPLC. When judged complete, the reaction was diluted with EtOAc (100 ml) and washed with sat. aq. NaHCO3 (5×30 ml), brine (30 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The yellow solid was purified by column chromatography using 5% MeOH in CH2Cl2 as the eluent. The product was dried overnight in vacuo giving ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylate in 70% yield.

Workup

  1. washwashed with sat. aq. NaHCO3 (5×30 ml), brine (30 ml)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe yellow solid was purified by column chromatography
  6. customThe product was dried overnight in vacuo

Sources & evidence

ORD record
ord-7ad28e6003144e34a8b89ccba300464e
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Linked notes

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