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Dimethylformamide → 5-[10-Chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-4-methylpyridine-2-carbonitrile

HRID 1628645
ノート
印刷プレビュー

反応式

HRID 1628645 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N:14]2[C:20]3=[N:21][C:22]4[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]([CH:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:23]=4[N:19]3[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:9][N:8]=1)(=O)=O.[CH3:36][N:37](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:28][C:27]1[C:22]2[N:21]=[C:20]3[N:14]([C:10]4[C:11]([CH3:13])=[CH:12][C:7]([C:36]#[N:37])=[N:8][CH:9]=4)[CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[C:23]=2[C:24]([CH:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[CH:25][CH:26]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 577860145-[10-Chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-4-methylpyridin-2-yl trifluoromethanesulfonate

生成物 1

HCID 577859415-[10-Chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-4-methylpyridine-2-carbonitrile収率 76%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 178418397
HCID 178418397、化合物
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

Under argon atmosphere a mixture of 5-[10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-4-methylpyridin-2-yl trifluoromethanesulfonate (Example 58; 285 mg, 0.537 mmol), zinc cyanide (94.5 mg, 0.805 mmol), tetrakis(triphenylphosphine)palladium(0) (62.1 mg, 0.0537 mmol) and N,N-dimethylformamide (2.7 mL) was stirred at 120° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a solid (166 mg, 0.407 mmol, 76%). Analytically pure material was obtained by recrystallization from ethyl acetate/n-hexane.

後処理

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-ac5aecb69f2c401e88ce4f3332de4cea
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785460B2

反応ノート

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