Diisopropylethylamine → 4-(4-Methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 13512

Reaction equation

HRID 13512 reaction equation
[CH3:1][NH:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20].CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.CC1(C)[NH:58][CH2:57][CH2:56][O:55]1>C1COCC1.C(OCC)(=O)C>[OH:55][CH2:56][CH2:57][NH:58][C:14]([C:10]1[CH:9]=[C:8]([O:7][C:6]2[CH:17]=[CH:18][C:3]([NH:2][CH3:1])=[C:4]([N+:19]([O-:21])=[O:20])[CH:5]=2)[CH:13]=[CH:12][N:11]=1)=[O:16]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 5506972,2-Dimethyl-oxazolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220404974-[4-(Methylamino)-3-nitrophenoxy]pyridine-2-carboxylic acid

Product 1

HCID 210373304-(4-Methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of the 4-(4-methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (1 eq) in dry THF, EDC-HCl (1.2 eq), HOAT (1.2 eq), and diisopropylethylamine (3 eq) were added. The suspension was stirred for 10 minutes whereupon 2,2-dimethyl-oxazolidine (1.1 eq) was added and the solution is allowed to stir overnight. The mixture was then diluted with ethyl acetate and washed with water. The aqueous layer was washed with ethyl acetate, the organic layers combined, dried over MgSO4, filtered, and concentrated. LCMS m/z 333.2 (MH+), tR=2.1 min.

Workup

  1. additionwere added
  2. additionwas added
  3. washwashed with water
  4. washThe aqueous layer was washed with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-050f194b2ccb435b9890b6c38cda17f2
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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