Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 6-(3,5-Difluorophenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]nicotinamide

HRID 602081노트

반응식

HRID 602081 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[F:19][C:20]([F:30])([F:29])[CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:28][CH:25]3[CH2:26][CH2:27][N:22]([CH2:21][C:20]([F:30])([F:19])[F:29])[CH2:23][CH2:24]3)=[O:15])=[CH:11][N:10]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

참가 물질

5

반응물 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178400021-(2,2,2-Trifluoroethyl)piperidin-4-amine hydrochlorideHCID 532230406-(3,5-Difluorophenyl)pyridine-3-carboxylic acid

생성물 1

HCID 597438396-(3,5-Difluorophenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]nicotinamide수율 7.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

6-(3,5-Difluoro-phenyl)-nicotinic acid (50 mg, 0.21 mmol), 1-(2,2,2-trifluoroethyl)piperidin-4-amine hydrochloride (48 mg, 0.22 mmol) N,N-diisopropylethylamine (0.296 mL, 1.69 mmol), HATU (101 mg, 0.26 mmol) in acetonitrile (5 mL) was shaken at room temperature for 12 h. The reaction mixture was concentrated and the crude reaction mixture purified by automated reversed phase chromatography to provide 6 mg (7%) of the title compound. 1H NMR (400 MHz, DMSO-d6) □ ppm 9.08 (1H, s), 8.47 (1H, d, J=7.0 Hz), 8.30 (1H, dd, J=8.4, 2.2 Hz), 8.19 (1H, d, J=8.1 Hz), 7.88 (2H, d, J=7.0 Hz), 7.36 (1H, t, J=10.1 Hz), 3.82 (1H, br. s.), 3.11-3.23 (2H, m), 2.95 (2H, d, J=11.0 Hz), 2.42-2.48 (2H, m), 1.76-1.87 (2H, m), 1.56-1.66 (2H, m).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude reaction mixture
  3. custompurified by automated reversed phase chromatography

출처 및 근거

ORD 기록
ord-1c47c0eabf614c1782aec5ee68f7982f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902373B2

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