Acetyl chloride → 6-(4-acetylpiperazin-1-yl)-N-((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)nicotinamide

HRID 711253노트

반응식

HRID 711253 반응식
[F:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[N:4][CH:5]=[C:6]([CH2:8][NH:9][C:10](=[O:23])[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:13][CH:12]=2)[CH:7]=1.CCN(C(C)C)C(C)C.[C:43](Cl)(=[O:45])[CH3:44]>C(Cl)Cl.C(OCC)(=O)C>[C:43]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:10]([NH:9][CH2:8][C:6]3[CH:7]=[C:2]([F:1])[C:3]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=4)=[N:4][CH:5]=3)=[O:23])=[CH:12][N:13]=2)[CH2:18][CH2:19]1)(=[O:45])[CH3:44]

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67208681N-((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)-6-(piperazin-1-yl)nicotinamide

생성물 1

HCID 565990266-(4-acetylpiperazin-1-yl)-N-((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)nicotinamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-((3-fluoro-2′-(trifluoromethyl)-[2,4′-bipyridin]-5-yl)methyl)-6-(piperazin-1-yl)nicotinamide 46-3 (35 mg, 0.076 mmol) and DIEA (27 μL, 0.155 mmol) in DCM (1.0 mL) was added acetyl chloride 46-4 (7 μL, 0.095 mmol). After 20 minutes stirring, the mixture was diluted with ethyl acetate, washed with water, and dried over Na2SO4. After evaporation of the solvents followed by preparative reverse phase HPLC separation gave 6-(4-acetylpiperazin-1-yl)-N-((3-fluoro-2′-(trifluoromethyl)-[2,4′-bipyridin]-5-yl)methyl)nicotinamide as a solid 46. MS m/z 503.2 (M+1). 1H NMR 400 MHz (CDCl3) δ 8.76 (d, 1H), 8.58 (d, 1H), 8.54-8.50 (m, 1H), 8.29 (bs, 1H), 8.07 (d, 1H), 7.97 (dd, 1H), 7.60 (dd, 1H), 6.62 (d, 1H), 4.63 (s, 2H), 3.72-3.65 (m, 4H), 3.61-3.55 (m, 4H), 2.10 (s, 3H).

후처리

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. customAfter evaporation of the solvents
  4. customfollowed by preparative reverse phase HPLC separation

출처 및 근거

ORD 기록
ord-48e0fdf73c734dca90ae7c0a5fbce75d
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181235B2

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