Triethylamine → Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetate

HRID 78655

反応式

HRID 78655 の反応式
[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH2:23])=[O:21])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.CCN(CC)CC.Cl[C:32](=[O:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1COCC1>[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH:23][C:32](=[O:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:21])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:15])=[O:16])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 594716323-Amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide

生成物 1

HCID 59472330Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetate収率 58.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide (2 g, 5.963 mmol) and Et3N (1.810 g, 2.493 mL, 17.89 mmol) were dissolved in THF (128.0 mL) and treated dropwise with ethyl 2-chloro-2-oxo-acetate (814.2 mg, 666.3 μL, 5.963 mmol) at 0° C. The reaction mixture was warmed slowly to room temperature and stirred for 1.5 h. The reaction mixture was filtered and grey solid washed with THF. The filtrate was evaporated to dryness azeotroping with acetonitrile. Then residue was then triturated with acetonitrile to give the product as a yellow solid (1.52 g, 58%); 1H NMR (400 MHZ, DMSO) d 1.19 (m, 6H), 1.32 (m, 3H), 3.34 (m, 1H), 4.32 (m, 2H), 7.88 (m, 2H), 8.56 (m, 2H), 9.07 (s, 1H), 10.95 (s, 1H) and 11.05 (s, 1H) ppm; MS (ES+) 436.32

後処理

  1. filtrationThe reaction mixture was filtered
  2. washgrey solid washed with THF
  3. customThe filtrate was evaporated to dryness
  4. customazeotroping with acetonitrile
  5. customThen residue was then triturated with acetonitrile

出典と根拠

ORDレコード
ord-4b4f714610f449a0801f1607f809f9fe
出典データセット
uspto-grants-2014_09
特許番号
US08841308B2

関連ノート

読み込み中…