1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

HRID 913269Notes

Reaction equation

HRID 913269 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.O.O[N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30]C=2N=N1.CN(C)CCCN=C=NCC.C1(CCN)CC1>ClCCl>[CH:28]1([CH2:27][CH2:26][NH:22][C:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])[CH2:29][CH2:30]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 64157626-chloropyridazine-3-carboxylic AcidHCID 10240761Cyclopropaneethanamine

Product 1

HCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamideYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-chloropyridazine-3-carboxylic acid (15.8 mmol) in dichloromethane (95 mL) was added diisopropylethylamine (46.7 mmol), 1-hydroxybenzotriazole monohydrate (23.7 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (23.7 mmol) under nitrogen atmosphere at ambient temperature. The resulting mixture was stirred for 15 minutes and 2-cyclopropylethylamine (20.2 mmol) was added. After stirring for 36 hours at ambient temperature, the reaction mixture was diluted with dichloromethane (100 mL), then washed with water and dried over anhydrous Na2SO4. The solvent was removed in vacuo. Purification via column chromatography (30% ethyl acetate in hexanes) afforded the title compound (8.70 mmol). Yield 55%.

Workup

  1. stirringAfter stirring for 36 hours at ambient temperature
  2. washwashed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed in vacuo
  5. customPurification via column chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b7ace317900842499eb265d7784e79f3
Source dataset
uspto-grants-2011_09
Patent number
US08026360B2

Reaction notes

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