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Hydrochloric Acid → 4-{[(6-Chloro-3,5-dicyano-4-phenylpyridin-2-yl)thio]methyl}-N-methylpyridine-2-carboxamide

HRID 1500108
ノート
印刷プレビュー

反応式

HRID 1500108 の反応式
N[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[C:28]#[N:29].N(OCCC(C)C)=O.[ClH:38]>C(#N)C.[Cu](Cl)Cl>[Cl:38][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[C:28]#[N:29]
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 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 565920084-{[(6-Amino-3,5-dicyano-4-phenylpyridin-2-yl)sulfanyl]methyl}-N-methylpyridine-2-carboxamide

生成物 1

HCID 582973474-{[(6-Chloro-3,5-dicyano-4-phenylpyridin-2-yl)thio]methyl}-N-methylpyridine-2-carboxamide

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒2 回
HCID 6342
Acetonitrile
溶媒

反応条件

温度
60 °C

実験手順

1.42 g (3.55 mmol) of the compound from Example 24A are initially charged in 30 ml of acetonitrile, 0.96 ml (7.10 mmol) of isopentyl nitrite and 0.95 g (7.10 mmol) of copper(II) chloride are added and the mixture is stirred at 60° C. for 5 hours. Once more, the same amount of copper(II) chloride is added and the mixture is stirred at 60° C. overnight. 7 ml of 1N hydrochloric acid are added, the mixture is extracted three times with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. The residue is purified by preparative HPLC (with 0.1% TFA added).

後処理

  1. stirringthe mixture is stirred at 60° C. overnight
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by preparative HPLC (with 0.1% TFA added)

出典と根拠

ORDレコード
ord-802e8d14fcf442c1a1555550314bdb5e
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09205077B2

反応ノート

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