1,2-Dichloroethane → 1-cyclobutyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}hexahydro-1H-1,4-diazepine

HRID 2261223ノート

反応式

HRID 2261223 の反応式
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[CH:35]1([N:39]2[CH2:45][CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36]1>CN(C=O)C.O.C(N(CC)CC)C>[CH:35]1([N:39]2[CH2:45][CH2:44][CH2:43][N:42]([C:13]([C:12]3[CH:11]=[CH:10][C:9]([B:4]4[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]4)=[CH:17][CH:16]=3)=[O:15])[CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36]1

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 574239521-Cyclobutyl-1,4-diazepane dihydrochloride

生成物 1

HCID 669304171-cyclobutyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}hexahydro-1H-1,4-diazepine収率 43.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.24 g) in dry DMF (30 ml) was treated with EDC (1.48 g) and HOBT (0.67 g). The reaction mixture was stirred at rt for 5 min, followed by the addition of 1-(cyclobutyl)hexahydro-1H-1,4-diazepine dihydrochloride (D4) (1.13 g) and triethylamine (2.7 ml). The mixture was stirred at rt overnight. The reaction mixture was then poured into water (250 ml) and extracted with EtOAc (2×35 ml). The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2×30 ml) followed by water (5×30 ml). After drying (magnesium sulphate) the solution was evaporated to give the title compound (D7) as an oil (0.84 g).MS electrospray (+ve ion) 385 (MH+).

後処理

  1. stirringThe mixture was stirred at rt overnight
  2. extractionextracted with EtOAc (2×35 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2×30 ml)
  4. dry with materialAfter drying (magnesium sulphate) the solution
  5. customwas evaporated

出典と根拠

ORDレコード
ord-bb53c593a28f4463b0096302bb7243e4
出典データセット
uspto-grants-2010_12
特許番号
US07846922B2

反応ノート

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