Aniline → HC-030031

HRID 44417

反応式

HRID 44417 の反応式
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].CCN(C(C)C)[CH:21]([CH3:23])[CH3:22].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH:21]([CH3:23])[CH3:22])=[CH:30][CH:29]=3)=[O:17])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

参加物

8

反応物 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69550AcefyllineHCID 81531Diisopropylethylamine

生成物 1

HCID 1150897HC-030031収率 41%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To the suspension of theophylline-7-acetic acid (101, 32.5 g, 0.136 mol) in anhydrous DMF (400 mL), was added DIPEA (54 mL, 0.31 mol) at 0° C. The neat aniline (102, 20.4 mL, 0.143 mol) was added followed by addition of DMAP (19.2 g, 0.16 mol) and EDCI (30.1 g, 0.16 mol). The reaction mixture was warmed to room temperature over 18 h, then stirred at 40-43° C. for 1.5 days. The reaction mixture was diluted with CH2Cl2 (1.8 L), washed with H2O (0.7 L), 10% citric acid (0.5 L), NaHCO3 (saturated, 0.6 L), brine, dried over Na2SO4 and concentrated in vacuo and crystallized from ethyl acetate/hexanes to yield compound 200 (41%, 19.8 g): MS (APCI) m/z: 356.2 [M+H]+. Anal. Calcd. for C18H21N5O3: C, 60.83; H, 5.96; N, 19.71. Found: C, 60.53; H, 5.97; N, 19.76.

後処理

  1. washwashed with H2O (0.7 L), 10% citric acid (0.5 L), NaHCO3 (saturated, 0.6 L), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customcrystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-ce3ea129c544445ab7e1ab343833eaf5
出典データセット
uspto-grants-2013_09
特許番号
US08541423B2

関連ノート

読み込み中…