Nitrogen mustard hydrochloride → HCID 178480776、化合物

HRID 20313

反応式

HRID 20313 の反応式
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:7][CH2:8]Cl)[CH3:6].[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:24]([NH2:25])=[CH:23][NH:22][N:21]=2)=[O:19])=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]([C:20]2[C:24]([N:25]3[CH2:8][CH2:7][N:5]([CH3:6])[CH2:4][CH2:3]3)=[CH:23][NH:22][N:21]=2)=[O:19])=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 5935Nitrogen mustard hydrochlorideHCID 81531DiisopropylethylamineHCID 178508056HCID 178508056、化合物

生成物 1

HCID 178480776HCID 178480776、化合物収率 19.8%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
200 °C

実験手順

Bis(2-chloroethyl)methylamine hydrochloride (97 mg; 0.5 mmol) was added to a stirred solution of 4-amino-1H-pyrazole-3-carboxylic acid (4-fluoro-phenyl)-amide (100 mg; 0.45 mmol), tetrabutylammonium iodide (20 mg; 0.045 mmol) and diisopropyethylamine (200 ul) 1.13 mmol) in DMF (5 ml), and the resulting mixture was heated at 200° C. (100 W) for 30 minutes in a CEM Discover™ microwave synthesiser. The DMF was removed under vacuum, then purified by flash column chromatography, eluting with dichloromethane/methanol/acetic acid/water (90:18:3:2). Product containing fractions were combined and evaporated, treated with HCl in ethyl acetate and then re-evaporated with toluene (2×20 ml) to give an off white solid (27 mg). (LC/MS: Rt 1.64, [M+H]+ 378).

後処理

  1. customThe DMF was removed under vacuum
  2. custompurified by flash column chromatography
  3. washeluting with dichloromethane/methanol/acetic acid/water (90:18:3:2)
  4. additionProduct containing fractions
  5. customevaporated
  6. additiontreated with HCl in ethyl acetate
  7. customre-evaporated with toluene (2×20 ml)

出典と根拠

ORDレコード
ord-76e6391191d14e0d8af31b3131bb0856
出典データセット
uspto-grants-2010_06
特許番号
US07745638B2

関連ノート

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