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Cyclohexanecarbonyl chloride → (R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(cyclohexyl)methanone

HRID 1689968
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HRID 1689968 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.[CH:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C.C(N(CC)C(C)C)(C)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:25]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:26])[CH2:14][C@H:13]2[CH3:18])=[N:4][N:3]=1
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참가 물질

6

반응물 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 57581473(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine

생성물 1

HCID 57581516(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(cyclohexyl)methanone

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매
HCID 81531
Diisopropylethylamine
용매

실험 절차

(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine (JK-2, 752 mg, 2.86 mmol) was dissolved in DMF (8 mL) and N,N-diisopropylethylamine (1.5 mL). Cyclohexanecarbonyl chloride (0.498 mL, 3.72 mmol) was added and the mixture stirred at rt for 16 hours. The reaction was taken up in ethyl acetate (80 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-75% ethyl acetate gave an off-white foam. MS (M+H)+=373.1.

후처리

  1. washwashed with aqueous K2CO3 (10%), water, and saturated sodium chloride
  2. dry with materialThe organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

출처 및 근거

ORD 기록
ord-37c7b19d745947ea99785547781d23c8
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153633B2

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