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

HRID 1433585

Reaction equation

HRID 1433585 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-d4be9d575dae478c84c8674a87194404
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Linked notes

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