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N'-(4-benzyloxy-3-cyano-pyridin-2-yl)-2-cyclopropylacetohydrazide → 7-Chloro-3-(cyclopropylmethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carbonitrile

HRID 1428487
ノート
印刷プレビュー

反応式

HRID 1428487 の反応式
[C:1]([C:3]1[C:4]([NH:17][NH:18][C:19](=O)[CH2:20][CH:21]2[CH2:23][CH2:22]2)=[N:5][CH:6]=[CH:7][C:8]=1OCC1C=CC=CC=1)#[N:2].O(Cl)[Cl:26].[P+5]>ClCCCl.C(Cl)Cl>[Cl:26][C:8]1[CH:7]=[CH:6][N:5]2[C:19]([CH2:20][CH:21]3[CH2:23][CH2:22]3)=[N:18][N:17]=[C:4]2[C:3]=1[C:1]#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 66784643N'-(4-benzyloxy-3-cyano-pyridin-2-yl)-2-cyclopropylacetohydrazideHCID 178479711HCID 178479711、化合物

生成物 1

HCID 574595937-Chloro-3-(cyclopropylmethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carbonitrile収率 64.3%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of D4 (1.4 g, 4.343 mmol) and phosphorous(V)oxychloride (0.810 ml, 8.686 mmol) in DCE (15 ml) was heated at 150° C. under microwave irradiation for 5 min. After cooling, the mixture was diluted with DCM and washed with NaHCO3 (aqueous sat. solution). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D5 (0.650 g, 64%).

後処理

  1. temperatureAfter cooling
  2. washwashed with NaHCO3 (aqueous sat. solution)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent)
  7. customThe desired fractions were collected
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d701d864225c4df19e61d135e8ccc734
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08937060B2

反応ノート

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