1,2-Dichloroethane → N'-[2-(6-bromopyridin-2-yl)acetyl]cyclopropanecarbohydrazide

HRID 386080ノート

反応式

HRID 386080 の反応式
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH:26]1([C:29]([NH:31][NH2:32])=[O:30])[CH2:28][CH2:27]1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([NH:32][NH:31][C:29]([CH:26]2[CH2:28][CH2:27]2)=[O:30])=[O:11])[CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81396CyclopropanecarbohydrazideHCID 81531DiisopropylethylamineHCID 468357142-(6-Bromopyridin-2-yl)acetic acid

生成物 1

HCID 59525662N'-[2-(6-bromopyridin-2-yl)acetyl]cyclopropanecarbohydrazide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(6-Bromopyridin-2-yl)acetic acid (Example 235, Step 2) (41% wt, 1.50 g, 2.85 mmol), EDC (1.64 g, 8.54 mmol), HOBT (872 mg, 5.69 mmol), and cyclopropanecarboxylic acid hydrazide (570 mg, 5.69 mmol) were combined in DMF (15 mL), and DIEA (994 μL, 5.69 mmol) was added. The reaction was stirred overnight at room temperature. After evaporation of the DMF, the residue was diluted with water and extracted with 5:1 CH2Cl2:MeOH (3×). The combined organic layers were dried (MgSO4), filtered, and evaporated. The solid residue was triturated with CH2Cl2 and filtered to isolate the title compound as a colorless solid.

後処理

  1. customAfter evaporation of the DMF
  2. additionthe residue was diluted with water
  3. extractionextracted with 5:1 CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue was triturated with CH2Cl2
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-423767529ffe4003869c2da08357e86f
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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