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

HRID 377406노트

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HRID 377406 반응식
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]([C:26]3[CH:31]=[CH:30][C:29](F)=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:33][CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.[C:41](=[O:44])([O-:43])[O-:42].[K+].[K+].[OH2:47]>CN(C=O)C>[OH2:8].[C:24]([OH:25])(=[O:47])[C:41]([OH:43])=[O:44].[C:41]([OH:42])(=[O:44])[C:7]([OH:8])=[O:47].[C:24]([OH:25])(=[O:47])[C:41]([OH:43])=[O:44].[N:36]1([CH2:35][CH2:34][NH:33][C:29]2[CH:30]=[CH:31][C:26]([C:24]([C:16]3[C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[S:19][C:15]=3[C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:10][CH:11]=3)=[O:25])=[CH:27][CH:28]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1

참가 물질

6

반응물 4

HCID 962WaterHCID 13441-PyrrolidineethanamineHCID 11430Potassium CarbonateHCID 107182054-Fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

생성물 1

HCID 211829432-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[[2-(1-Pyrrolidinyl)ethyl]-amino]phenyl Ketone Trioxalate Hydrate수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a53266674cf4a459283c908c2ca02c2
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025382

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