Dimethylamine, hydrochloride → 5-(5-Cyanopyridin-3-ylethynyl)-2-fluoro-N,N-dimethylbenzamide

HRID 606898ノート

反応式

HRID 606898 の反応式
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)C(C)C)(C)C.[C:14]([C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24]2[CH:25]=[CH:26][C:27]([F:33])=[C:28]([CH:32]=2)[C:29]([OH:31])=O)[CH:19]=[N:20][CH:21]=1)#[N:15].O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[C:14]([C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24]2[CH:25]=[CH:26][C:27]([F:33])=[C:28]([CH:32]=2)[C:29]([N:3]([CH3:4])[CH3:2])=[O:31])[CH:19]=[N:20][CH:21]=1)#[N:15]

参加物

7

反応物 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 670476775-(5-Cyanopyridin-3-ylethynyl)-2-fluorobenzoic acid

生成物 1

HCID 670483405-(5-Cyanopyridin-3-ylethynyl)-2-fluoro-N,N-dimethylbenzamide収率 63.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Add N-(3-dimethylaminopropyl)-N-ethylcarbodiamide hydrochloride (120 mg, 0.62 mmol) to a mixture of dimethylamine hydrochloride (51 mg, 0.62 mmol), N,N-diisopropylethylamine (108 μL, 0.62 mmol), 5-(5-cyanopyridin-3-ylethynyl)-2-fluorobenzoic acid, (prepared as described in EXAMPLE 120), (150 mg, 0.56 mmol) and 1-hydroxybenzotriazole hydrate (76 mg, 0.56 mmol) in N,N-dimethylformamide (2 mL), and stir for 2 h. Dilute the reaction mixture with ethyl acetate and an aqueous saturated solution of sodium bicarbonate and separate the layers. Extract the aqueous phase once with ethyl acetate. Extract the combined organic phases once with an aqueous saturated solution of sodium chloride, dry (sodium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 30:70 to 50:50 with ethyl acetate:hexanes, to give the title compound as a white solid (104 mg, 63%).

後処理

  1. customan aqueous saturated solution of sodium bicarbonate and separate the layers
  2. extractionExtract the aqueous phase once with ethyl acetate
  3. extractionExtract the combined organic phases once with an aqueous saturated solution of sodium chloride
  4. dry with materialdry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by silica gel chromatography
  8. washeluting with 30:70 to 50:50 with ethyl acetate

出典と根拠

ORDレコード
ord-dcad96ef49e84c3c9c8377f8c23d37a1
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

反応ノート

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