1,2-Dichloroethane → N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide

HRID 1257541ノート

反応式

HRID 1257541 の反応式
[Cl-].[Na+].[Na+].[Na+].[Cl-].[Cl-].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[C:16]([CH:20]=[C:21]([CH:23]=[CH2:24])[CH:22]=2)[C:17]([OH:19])=O)=[N:12][CH:13]=1.Cl.[F:26][C:27]1[CH:28]=[CH:29][C:30]([C@H:33]([NH2:35])[CH3:34])=[N:31][CH:32]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:26][C:27]1[CH:28]=[CH:29][C:30]([C@H:33]([NH:35][C:17](=[O:19])[C:16]2[CH:20]=[C:21]([CH:23]=[CH2:24])[CH:22]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][N:12]=3)[CH:15]=2)[CH3:34])=[N:31][CH:32]=1

参加物

9

反応物 7

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 23615961Tri-sodium chlorideHCID 66690953(1R)-1-(5-fluoropyridin-2-yl)ethan-1-amine hydrochlorideHCID 668957363-(5-Methyl-2-pyridinyl)-5-vinylbenzoic acid

生成物 1

HCID 66895503N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide収率 52.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of tri-sodium chloride adduct of 3-(5-methyl-2-pyridinyl)-5-vinylbenzoic acid (2.5 g, 6.0 mmol) in N,N-dimethylformamide (20 mL) were added (1R)-1-(5-Fluoropyridin-2-yl)ethanamine hydrochloride (1.60 g, 7.5 mmol), EDC (2.02 g, 10.5 mmol), HOAT (0.25 g, 1.8 mmol) and triethylamine (3.36 mL, 24 mmol). The reaction mixture was stirred at ambient temperature for 18 h. Saturated aqueous sodium bicarbonate was added. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→100% ethyl acetate) gave the title compound (1.14 g). MS 362.1 (M+1).

後処理

  1. extractionThe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% hexanes→100% ethyl acetate)

出典と根拠

ORDレコード
ord-d514aa66fb404d55a055e81d3ee2edb5
出典データセット
uspto-grants-2013_06
特許番号
US08461185B2

反応ノート

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