Triethylamine → N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)-6-methylnicotinamide

HRID 572203노트

반응식

HRID 572203 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:10][C:11]2[CH:16]=[N:15][CH:14]=[C:13]([Cl:17])[N:12]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][N:20]=1.Cl.CN(C)CCCN=C=NCC.N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Cl:17][C:13]1[N:12]=[C:11]([NH:10][C@H:8]([C:4]2[CH:3]=[C:2]([NH:1][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][C:19]([CH3:18])=[N:20][CH:21]=3)[CH:7]=[CH:6][CH:5]=2)[CH3:9])[CH:16]=[N:15][CH:14]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 1378606-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 25218447(S)-N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amine

생성물 1

HCID 25218451N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)-6-methylnicotinamide수율 86.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of N-[(1S)-1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (300 mg, 1.2 mmol), 6-methylnicotinic acid (182 mg, 1.32 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (277 mg, 1.45 mmol), 4-pyrrolidinopyridine (36 mg, 0.24 mmol) and triethylamine (0.34 mL, 2.4 mmol) in dichloromethane (6 mL) was stirred at room temperature for 72 hours. After this time the mixture was diluted with ethyl acetate (20 mL), washed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL), dried (Na2SO4) and concentrated under reduced pressure to give a yellow oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)-6-methylnicotinamide (380 mg, 86%) as a white solid.

후처리

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow oil which
  5. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-fa1031100efd4302bb7262777a7ec514
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029386B2

반응 노트

불러오는 중…