Diethyl Ether → 4-(2-amino-3H-imidazol-4-yl)-2,3-dichloro-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

HRID 29790

反応式

HRID 29790 の反応式
[Cl:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH:10](O)[C:4]=2[C:3]=1[Cl:14].S(O)(O)(=O)=O.[NH2:20][C:21]1[NH:22][CH:23]=[CH:24][N:25]=1.CCOCC>CS(O)(=O)=O>[NH2:20][C:21]1[NH:25][C:24]([CH:10]2[CH2:9][CH2:8][NH:7][C:6](=[O:12])[C:5]3[NH:13][C:2]([Cl:1])=[C:3]([Cl:14])[C:4]2=3)=[CH:23][N:22]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 597892292,3-dichloro-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

生成物 1

HCID 597891934-(2-amino-3H-imidazol-4-yl)-2,3-dichloro-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
45 °C

実験手順

To a solution of 2,3-dichloro-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one (60 mg, 0.256 mmol), prepared as in reference 2, in methanesulfonic acid (0.5 mL) is added 2-aminoimidazole sulfate (40.5 mg, 0.153 mmol). The mixture is stirred at 45° C. overnight, cooled to room temperature and Et2O (5 mL) is added resulting in brown oil. After discarding the supernatant, the oil is purified by silica gel column chromatography and eluted with MeOH—CH2Cl2 to give 4-(2-amino-3H-imidazol-4-yl)-2,3-dichloro-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one; 1H NMR (Methanol-d4) δ 2.09-2.17 (m, 1H), 2.23-2.31 (m, 1H), 3.20-3.29 (m, 2H), 4.23 (t, 1H, J=3.6 Hz), 6.18 (s, 1H); m/z [M++1] 300.0.

後処理

  1. temperaturecooled to room temperature
  2. customresulting in brown oil
  3. customthe oil is purified by silica gel column chromatography
  4. washeluted with MeOH—CH2Cl2

出典と根拠

ORDレコード
ord-0c3cf8259ecf4237833c40d66f62a5fb
出典データセット
uspto-grants-2008_09
特許番号
US07423031B2

関連ノート

読み込み中…