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

HRID 386080노트

반응식

HRID 386080 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-423767529ffe4003869c2da08357e86f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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