1,2-Dichloroethane → (6-Chloro-pyridin-3-yl)-(4-isopropyl-piperazin-1-yl)-methanone

HRID 30464

反応式

HRID 30464 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl.[OH-].[Na+]>[NH3:3].[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:17]2[CH2:18][CH2:19][N:14]([CH:11]([CH3:13])[CH3:12])[CH2:15][CH2:16]2)=[O:8])=[CH:9][CH:10]=1

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 780131-IsopropylpiperazineHCID 792226-Chloronicotinic acid

生成物 2

HCID 222Ammonia収率 2%HCID 43420904(6-Chloro-pyridin-3-yl)-(4-isopropyl-piperazin-1-yl)-methanone収率 111.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of 6-chloronicotinic acid (0.985 g, 6.25 mmol) and 1-isopropyl-piperazine (1.50 g, 7.50 mmol) in DCM (100 mL) was added HOBt (1.20 g, 9.40 mmol), EDC (1.80 g, 9.40 mmol), and N-methyl morpholine (3.4 mL, 31.3 mmol). After 18 h the reaction was diluted with 1 N NaOH (50 mL) and extracted with DCM (3×50 mL). The organic extracts were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2: 2-4% 2 M NH3 in MeOH/DCM) gave the title compound as a solid (0.934 g, 56%).

後処理

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-93d41b1e83374a8195fa06817844aaee
出典データセット
uspto-grants-2008_09
特許番号
US07423147B2

関連ノート

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