Triethylamine → 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[2,3-d][1,3]oxazin-4-one

HRID 887731

反応式

HRID 887731 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13](Cl)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:20][C:21]1[N:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].C(N(CC)CC)C.CS(Cl)(=O)=O>C(#N)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:14][C:23](=[O:24])[C:22]4[CH:26]=[CH:27][CH:28]=[N:29][C:21]=4[N:20]=3)=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 31297Methanesulfonyl chlorideHCID 729302-Aminonicotinic acidHCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl Chloride

生成物 1

HCID 593555542-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyrido[2,3-d][1,3]oxazin-4-one収率 65%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

5-Trifluoromethyl-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid chloride (example 2, step 3) (800 mg) was added to a mixture of 2-aminonicotinic acid (356 mg) in acetonitrile (20 mL). The mixture was stirred for 10 minutes at room temperature and triethylamine (360 μL) was added and stirred for 15 minutes, before a second portion of triethylamine (720 μL) was added. After the mixture was stirred for further 15 minutes at room temperature, methanesulfonyl chloride (220 μL) was added. After stirring for 1.5 hours at room temperature, the reaction was quenched with water and extracted 2× with ethyl acetate, washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, chloroform/ethyl acetate=1:1, Rf=0.40) to afford 660 mg of the title compound of the formula

後処理

  1. additionwas added
  2. stirringAfter the mixture was stirred for further 15 minutes at room temperature
  3. stirringAfter stirring for 1.5 hours at room temperature
  4. customthe reaction was quenched with water
  5. extractionextracted 2× with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuum
  9. customThe residue was purified by column chromatography (silica 60, chloroform/ethyl acetate=1:1, Rf=0.40)

出典と根拠

ORDレコード
ord-c3e27e5f4bed4622a4d935d5c5ba3b28
出典データセット
uspto-grants-2012_08
特許番号
US08247431B2

関連ノート

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