2-Fluoro-4-iodoaniline → 4-(2-Fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

HRID 15971

반응식

HRID 15971 반응식
Cl[C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].[F:14][C:15]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:16]=1[NH2:17].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:14][C:15]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:16]=1[NH:17][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

참가 물질

5

반응물 3

HCID 1856942-Fluoro-4-iodoanilineHCID 2733832Lithium HexamethyldisilazideHCID 666732574-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

생성물 1

HCID 666740444-(2-Fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid수율 39.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (200 mg, 0.99 mmol) and 2-fluoro-4-iodoaniline (478 mg, 1.97 mmol) in THF (6.5 mL) at −78° C. was slowly added a solution of LiHMDS (3.00 mL, 3.00 mmol, 1 M solution in THF). After complete addition, the resulting mixture was slowly warmed to room temperature and stirred for 4 hours. The reaction mixture was quenched with 6 N aqueous HCl (8 mL) at 0° C., warmed to room temperature, and stirred for 1.5 hours. The precipitates were filtered, washed with water and ether, and triturated with ether to afford 158 mg (38%) of the desired product.

후처리

  1. additionAfter complete addition
  2. customThe reaction mixture was quenched with 6 N aqueous HCl (8 mL) at 0° C.
  3. temperaturewarmed to room temperature
  4. stirringstirred for 1.5 hours
  5. filtrationThe precipitates were filtered
  6. washwashed with water and ether
  7. customtriturated with ether

출처 및 근거

ORD 기록
ord-ea53a66d1fe7469b90f5841085c5c4dc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732616B2

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