Diisopropylethylamine → HCID 58230870、化合物

HRID 252237

反応式

HRID 252237 の反応式
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].CCN(C(C)C)C(C)C.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=1[OH:30]>C(Cl)Cl.C1COCC1.C(OCC)(=O)C>[OH:30][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:21]=1[NH:20][C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[C:25]([OH:27])=[O:26]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 1375664-Amino-3-hydroxybenzoic acidHCID 129025982-Methylpyridine-3-carbonyl chloride

生成物 1

HCID 58230870HCID 58230870、化合物収率 40.2%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

2-methyl nicotinoyl chloride (0.2 g, 0.00128 mols) is dissolved in 30 ml dry DCM and N,N′-Diisopropylethylamine (0.994 g, 0.00769 mols) is added slowly to the acid chloride solution at 0° C. under nitrogen atmosphere. A solution of 4-Amino-3-hydroxybenzoic acid (0.196 g, 0.00128 mols) in 10 ml dry THF is slowly added to the above solution at 0° C. The solution is then stirred at 0° C. for 30 mins and then at RT overnight. The reaction mixture is then diluted with 100 ml Ethyl acetate and stirred for 30 mins. The precipitated tarry material is filtered off over celite bed and the organic phase given 4×20 ml water wash, 2×10 ml brine wash dried over sodium sulfate and rotary evaporated to get the crude amide (140 mg) which is taken for the cyclisation step without further purification.

後処理

  1. customat RT
  2. customovernight
  3. stirringstirred for 30 mins
  4. filtrationThe precipitated tarry material is filtered off over celite bed
  5. washwash
  6. wash2×10 ml brine wash
  7. dry with materialdried over sodium sulfate
  8. customrotary evaporated

出典と根拠

ORDレコード
ord-68113f6b2507438c962f16b003e8b0f2
出典データセット
uspto-grants-2011_01
特許番号
US07868033B2

関連ノート

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