1-Hydroxybenzotriazole → 4-Chloro-2-[(cyclopropylmethyl)aminocarbonyl]pyridine

HRID 853452

Reaction equation

HRID 853452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.Cl.[NH2:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.Cl.C(N=C=NCCCN(CC)CC)C.ON1C2C=CC=CC=2N=N1>O.O1CCCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[O:10])[CH:3]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 2308904-Chloropyridine-2-carboxylic acidHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Product 1

HCID 348291214-Chloro-2-[(cyclopropylmethyl)aminocarbonyl]pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

4-Chloro-2-carboxypyridine (2.0 g), (aminomethyl)cyclopropane hydrochloride (1.7 g), 1-ethyl-3-(3-diethylaminopropyl)carbodiimide hydrochloride (WSC) (2.9 g), 1-hydroxybenzotriazole (HOBt) (2.3 g), triethylamine (2.1 ml) and tetrahydrofuran (30 ml) were stirred together at room temperature for 2 hours. Water was added, extraction was performed with ethyl acetate, and then silica gel was added to the extract and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel and purified by column chromatography (hexane:ethyl acetate=4:1, followed by 2:1) to obtain 1.5 mg of the target substance as a yellow oil.

Workup

  1. extractionextraction
  2. additionsilica gel was added to the
  3. extractionextract
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompurified by column chromatography (hexane:ethyl acetate=4:1, followed by 2:1)
  7. customto obtain 1.5 mg of the target substance as a yellow oil

Sources & evidence

ORD record
ord-b44104e3e2ff48f8a9281ae5cd0ece9f
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Linked notes

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