Methyl Picolinimidate → Tert-butyl 8-chloro-3-pyridin-2-yl[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate

HRID 592300노트

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HRID 592300 반응식
Cl.[Cl:2][C:3]1[C:4]([NH:16][NH2:17])=[N:5][CH:6]=[C:7]([CH:15]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CO[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=N>CO>[Cl:2][C:3]1[C:4]2[N:5]([C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:17][N:16]=2)[CH:6]=[C:7]([C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[CH:15]=1

참가 물질

4

반응물 2

HCID 152260Methyl PicolinimidateHCID 66690635Tert-butyl 5-chloro-6-hydrazinonicotinate hydrochloride salt

생성물 1

HCID 66690204Tert-butyl 8-chloro-3-pyridin-2-yl[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate수율 7.6%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
65 °C

실험 절차

To a solution of tert-butyl 5-chloro-6-hydrazinonicotinate hydrochloride salt (5.5 g, 17.4 mmol) in methanol (80 mL) was added methylpyridine-2-carboximidoate (4.73 g, 34.7 mmol). The mixture was heated to 65° C. After 2.5 h, the mixture was cooled to ambient temperature. The solid crashed out was filtered off and the filtrate was concentrated. Purification by silica gel chromatography (100% hexanes→60% hexanes/ethyl acetate) gave 0.44 g of the title compound and 1.3 g of a side product. The side product (1.3 g) was dissolved in methanol (28 mL) and acetic acid (0.53 mL) was added. The mixture was heated to 65° C. After 7 h, the reaction was cooled to ambient temperature and saturated aqueous sodium bicarbonate was added. The mixture was extracted with ethyl acetate (3×). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to give another 1.0 g of the title compound: LC-MS [M+1]=331.1.

후처리

  1. temperaturethe mixture was cooled to ambient temperature
  2. filtrationThe solid crashed out was filtered off
  3. concentrationthe filtrate was concentrated
  4. customPurification by silica gel chromatography (100% hexanes→60% hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-c4f9515de14c4ff28c1cabe0a418706c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238647B2

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