Ammonia → 4-Methyl-3-(1-morpholinophthalazin-6-yl)benzamide

HRID 2357595ノート

反応式

HRID 2357595 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:16][N:15]=[CH:14]2.N.O1CCOCC1.C([N:37](C(C)C)CC)(C)C>S(Cl)(Cl)=O.CCOC(C)=O>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:37])=[O:7])=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:16][N:15]=[CH:14]2

参加物

7

反応物 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 251930634-Methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid

生成物 1

HCID 118483714-Methyl-3-(1-morpholinophthalazin-6-yl)benzamide

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
70 °C

実験手順

4-Methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid (86 mg, 0.25 mmol) was dissolved in thionyl chloride (3.6 mL) and heated to 70° C. for 2 h. The reaction mixture was concentrated in vacuo before ammonia, 0.5 M in 1,4-dioxane (10 mL, 4.9 mmol) and diisopropylethylamine (0.2 mL, 1.2 mmol) were added. The reaction mixture was heated to 50° C. for 5 h and stirred overnight at RT. The reaction was diluted with 100 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were washed 3 times 75 mL of sodium bicarbonate (saturated, aqueous), combined, dried over sodium sulfate, and concentrated via rotovap to give a crude product. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 349(M+H)+.

後処理

  1. temperatureThe reaction mixture was heated to 50° C. for 5 h
  2. additionadded to an addition funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washThe organic layers were washed 3 times 75 mL of sodium bicarbonate (saturated, aqueous)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap
  7. customto give a crude product
  8. customThe crude was purified by chromatography

出典と根拠

ORDレコード
ord-c516d2b566654806b618e5d3770ff22d
出典データセット
uspto-grants-2010_07
特許番号
US07759337B2

反応ノート

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