Sodium Nitrate → (7-Bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)hydroxyiminoacetonitrile

HRID 1863997ノート

反応式

HRID 1863997 の反応式
[Br:1][C:2]1[C:3]([NH:15][CH2:16][CH3:17])=[C:4]([NH:9][C:10](=O)[CH2:11][C:12]#[N:13])[C:5]([Cl:8])=[N:6][CH:7]=1.BrC1C2N(CC)C(CC#N)=NC=2C(Cl)=NC=1.[N+:34]([O-])([O-])=[O:35].[Na+]>C(O)(=O)C>[Br:1][C:2]1[C:3]2[N:15]([CH2:16][CH3:17])[C:10]([C:11](=[N:34][OH:35])[C:12]#[N:13])=[N:9][C:4]=2[C:5]([Cl:8])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 24268Sodium NitrateHCID 45480183(7-Bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrileHCID 57973904N-[5-Bromo-2-chloro-4-(ethylamino)-3-pyridinyl]-2-cyanoacetamide

生成物 1

HCID 136380978(7-Bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)hydroxyiminoacetonitrile収率 114.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of N-[5-bromo-2-chloro-4-(ethylamino)-3-pyridinyl]-2-cyanoacetamide III, (458 g, 1.45 mol) in glacial acetic acid (4.6 L) was heated to 100° C. After 3 h, LC/MS analysis indicated that the conversion to (7-bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile (IV) was completed. After allowing to cool to ambient temperature, the reaction was charged with sodium nitrate (230 g, 3.34 mol) in portions. Vigorous gas evolution and foaming was observed together with a ˜10° C. exotherm. After stirring at ambient temperature for 16 h, the solid was collected by filtration and dried to a constant weight to give 545 g of the desired product (V) as a light yellow solid. This was used in the next step without further purification. MS (ES+) m/z 328 (M+H)+.

後処理

  1. customwas observed together with a ˜10° C.
  2. filtrationthe solid was collected by filtration
  3. customdried to a constant weight

出典と根拠

ORDレコード
ord-9183eef1cd2e45eb917071992ad04803
出典データセット
uspto-grants-2009_12
特許番号
US07625890B2

反応ノート

読み込み中…