Triethylamine → (R)-N-Benzyl-2-chloro-N-(2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-ylamino)ethyl)propanamide

HRID 2093363ノート

反応式

HRID 2093363 の反応式
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[N:13]=[N:14][C:15]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:16]([CH3:19])[C:17]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:27][C@H:28]([CH3:32])[C:29](O)=[O:30].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][NH:11][C:12]1[N:13]=[N:14][C:15]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:16]([CH3:19])[C:17]=1[CH3:18])[C:29](=[O:30])[C@H:28]([Cl:27])[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27245402-Chloropropionic acid, (+)-HCID 67320023N1-Benzyl-N2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

生成物 1

HCID 58359251(R)-N-Benzyl-2-chloro-N-(2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-ylamino)ethyl)propanamide収率 74.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sequentially treat a solution of N1-benzyl-N2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine (4.90 g, 13.98 mmol) in CH2Cl2 (70 mL) with (R)-(+)-2-chloropropionic acid (1.84 mL, 20.97 mmol), triethylamine (2.92 mL, 20.97 mmol), HOBT (3.21 g, 20.97 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.02 g, 20.97 mmol). Stir the resulting mixture at ambient temperature overnight. Wash the reaction mixture with saturated aqueous NaHCO3. Extract the aqueous layer with CH2Cl2. Combine the organic layers, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (20% EtOAc in hexanes) to afford the title compound as a yellow foam (4.59 g, 74%). ES/MS m/z 441.2 (M+1).

後処理

  1. washWash the reaction mixture with saturated aqueous NaHCO3
  2. extractionExtract the aqueous layer with CH2Cl2
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash silica gel chromatography (20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-7125993a82994698845e09efa4c8d118
出典データセット
uspto-grants-2013_05
特許番号
US08445493B2

反応ノート

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