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

HRID 711253ノート

反応式

HRID 711253 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-48e0fdf73c734dca90ae7c0a5fbce75d
出典データセット
uspto-grants-2015_11
特許番号
US09181235B2

反応ノート

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