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

HRID 1915689

反応式

HRID 1915689 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-43ee4ff89b9a4982a326b71e8dbd634a
出典データセット
uspto-grants-2013_12
特許番号
US08614330B2

関連ノート

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