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

HRID 1010319노트

반응식

HRID 1010319 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8db7b62bbbeb4b67805bf3760aae6503
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973160B2

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