Water → (R)-Methyl 6-(1-amino-4-methyl-1-oxopentan-2-ylamino)-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate

HRID 711487노트

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HRID 711487 반응식
Cl[C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)[N:3]=1.[NH2:20][C@H:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([NH2:24])=[O:23].O>CC(N(C)C)=O>[NH2:24][C:22](=[O:23])[C@H:21]([NH:20][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)[N:3]=1)[CH2:25][CH:26]([CH3:28])[CH3:27]

참가 물질

5

반응물 3

HCID 962WaterHCID 7271815(R)-2-Amino-4-methylpentanamideHCID 58317582methyl 6-chloro-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate

생성물 1

HCID 67237475(R)-Methyl 6-(1-amino-4-methyl-1-oxopentan-2-ylamino)-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate수율 11%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
150 °C

실험 절차

A mixture of methyl 6-chloro-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate (82.9 mg, 0.300 mmol) and (R)-2-amino-4-methylpentanamide (39.0 mg, 0.300 mmol) in DMA (2 mL) was stirred at 150° C. for 12 h. Water was subsequently added and the mixture was extracted with EtOAc. The organic layers were washed with saturated aq NaHCO3, water, and brine, were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, EtOAc) to give the title compound as a yellow oil (11.7 mg, 11%).

후처리

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layers were washed with saturated aq NaHCO3, water, and brine
  3. dry with materialwere dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (SiO2, EtOAc)

출처 및 근거

ORD 기록
ord-84301540e6f24f8184dd6d90de1a1b9e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

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