Benzoyl chloride → (R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

HRID 1689954노트

반응식

HRID 1689954 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[CH3:18])=[N:4][N:3]=1.C(N(CC)C(C)C)(C)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:35])[CH2:14][C@H:13]2[CH3:18])=[N:4][N:3]=1

참가 물질

6

반응물 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 57581473(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine

생성물 1

HCID 57581487(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine (2.94 g, 11.94 mmol) was dissolved in dry DMF (24 mL) and N,N-diisopropylethylamine (3.12 mL, 17.9 mmol). Benzoyl chloride (1.43 mL, 12.3 mmol) was added dropwise and the reaction stirred at rt for 16 hours. The reaction was taken up in ethyl acetate (200 mL), and washed with aqueous K2CO3 (10%), water, and then saturated sodium chloride. The organic phase was dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-70% ethyl acetate gave an off-white solid. MS (M+H)+=367.

후처리

  1. washwashed with aqueous K2CO3 (10%), water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

출처 및 근거

ORD 기록
ord-21448d06d95e4bb3b4ebe30b50cbe2bc
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153633B2

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