Sodium hydride → 5-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine

HRID 1357005노트

반응식

HRID 1357005 반응식
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[H-].[Na+].[CH:12]1([O:17][C:18]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[N:21][NH:22][CH:23]3Cl)[CH2:16][CH2:15][CH2:14][CH2:13]1>CN(C)C=O>[CH:12]1([O:17][C:18]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[N:21][N:22]=[C:23]3[CH2:8][C:7]2[C:6]([Cl:9])=[CH:5][N:4]=[CH:3][C:2]=2[Cl:1])[CH2:13][CH2:14][CH2:15][CH2:16]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 185048005-cyclopentyloxy-1-chloro-6-methoxy-2H-phthalazine

생성물 1

HCID 98659165-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine수율 57.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3,5-dichloro-4-methyl-pyridine (13.86 g, 85.56 mmoles) in dry dimethylformamide (100 ml) was added, under nitrogen and stirring, with 55% NaH (3.73 g, 85.56 mmoles). The mixture was stirred for 1 hour then added with a solution of 5-cyclopentyloxy-1-chloro-6-methoxy-2H-phthalazine (7.95 g, 28.52 mmoles), obtained as described in example 7, in dry dimethylfomamide (70 ml). The mixture was left to stand for one night, quenched with water, diluted with water and extracted methyl aceate. The extract was washed with water and anhydrified over Na2SO4, then evaporated to dryness. The residue was flash chromatographed (eluent:petrolatum/ethyl acetate 1:1) to give 6.58 g of the title product (yield: 57%).

후처리

  1. customobtained
  2. waitThe mixture was left
  3. waitto stand for one night
  4. customquenched with water
  5. additiondiluted with water
  6. extractionextracted methyl aceate
  7. washThe extract was washed with water
  8. customevaporated to dryness
  9. customchromatographed (eluent:petrolatum/ethyl acetate 1:1)

출처 및 근거

ORD 기록
ord-67c84279d39146c5a9058e0f50976f22
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589951B1

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