Acetohydrazide → N'-acetyl-3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazide

HRID 335193ノート

反応式

HRID 335193 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([OH:18])=O)[N:13]=2)=[N:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.[C:57]([NH:60][NH2:61])(=[O:59])[CH3:58]>C(#N)C.C1COCC1>[C:57]([NH:60][NH:61][C:16](=[O:18])[CH2:15][CH2:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[C:4]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[S:10][CH:11]=1)(=[O:59])[CH3:58]

参加物

8

反応物 5

HCID 14039AcetohydrazideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 577426713-(2-(5-Bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoic acid

生成物 1

HCID 86631510N'-acetyl-3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazide収率 127%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoic acid (0.300 g, 0.714 mmol), HOBT-H2O (0.164 g, 1.07 mmol), DIEA (0.261 mL, 1.50 mmol), EDCI (0.205 g, 1.07 mmol), and acetohydrazide (0.106 g, 1.43 mmol) in 10 mL acetonitrile and 2 mL THF was stirred at 50° C. for 3 hours and then overnight at ambient temperature. The mixture was concentrated and diluted with CH2Cl2, washed with saturated aqueous NaHCO3, dried over Na2SO4, and concentrated to provide the title compound (0.431 g, 127% yield) that was carried directly on to the next step.

後処理

  1. customovernight
  2. customat ambient temperature
  3. concentrationThe mixture was concentrated
  4. additiondiluted with CH2Cl2
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-6fc7da30f36e4f1ca850d165753c2ba1
出典データセット
uspto-grants-2014_11
特許番号
US08883828B2

反応ノート

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