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

HRID 386080Notes

Reaction equation

HRID 386080 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-423767529ffe4003869c2da08357e86f
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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