Water → 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[[2-(1-Pyrrolidinyl)ethyl]-amino]phenyl Ketone Trioxalate Hydrate

HRID 1070334ノート

反応式

HRID 1070334 の反応式
O.[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[C:8]([OH:13])(=[O:12])[C:9]([OH:11])=[O:10].[N:14]1([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[S:32][C:31]4[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=4[C:29]=3[C:37]([C:39]3[CH:44]=[CH:43][C:42](OCCCCN4CCCC4)=[CH:41][CH:40]=3)=[O:38])=[CH:24][CH:23]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.[NH2:55][CH2:56][CH2:57][N:58]1[CH2:62][CH2:61][CH2:60][CH2:59]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[OH2:4].[C:8]([OH:13])(=[O:12])[C:9]([OH:11])=[O:10].[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[N:58]1([CH2:57][CH2:56][NH:55][C:42]2[CH:41]=[CH:40][C:39]([C:37]([C:29]3[C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[S:32][C:28]=3[C:25]3[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)=[CH:23][CH:24]=3)=[O:38])=[CH:44][CH:43]=2)[CH2:62][CH2:61][CH2:60][CH2:59]1

参加物

6

反応物 4

HCID 962WaterHCID 13441-PyrrolidineethanamineHCID 11430Potassium CarbonateHCID 211827494-[4-(1-Pyrrolidinyl)butoxy]phenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone Dioxalate Hydrate

生成物 1

HCID 211829432-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[[2-(1-Pyrrolidinyl)ethyl]-amino]phenyl Ketone Trioxalate Hydrate収率 130.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

4-Fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl)benzo[b]thiophen-3-yl ketone (Example 145, Part A) (1.1 g; 2.5 mmol) was combined with 1.6 mL (12.3 mmol) of 1-(2-aminoethyl)pyrrolidine and 1.0 g (7.4 mmol) of potassium carbonate in 2 mL of dry DMF. The mixture was heated in an oil bath maintained at 130° C. for 18 h. After cooling to room temperature, the mixture was poured into 150 mL of water and stirred for 0.5 h. The product was isolated by filtration and washed with fresh water. The title compound (0.9 g; 68% yield) was purified by flash chromatography on silica gel, eluting with a gradient of hexanes(75-15%)/Et3N(5%)/THF(20-80%). Conversion to the trioxalate was effected as in Example 137, Part E.

後処理

  1. temperatureThe mixture was heated in an oil bath
  2. temperatureAfter cooling to room temperature
  3. customThe product was isolated by filtration
  4. washwashed with fresh water

出典と根拠

ORDレコード
ord-bb570f7e48d247598da13b3dd544e2bf
出典データセット
uspto-grants-2001_06
特許番号
US06251921B1

反応ノート

読み込み中…