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

HRID 1689954ノート

反応式

HRID 1689954 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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.

後処理

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

出典と根拠

ORDレコード
ord-21448d06d95e4bb3b4ebe30b50cbe2bc
出典データセット
uspto-grants-2012_04
特許番号
US08153633B2

反応ノート

読み込み中…