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

HRID 1863997노트

반응식

HRID 1863997 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-9183eef1cd2e45eb917071992ad04803
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625890B2

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