Water → HCID 21182943, compound

HRID 1070334Notes

Reaction equation

HRID 1070334 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 21182943HCID 21182943, compoundYield 130.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bb570f7e48d247598da13b3dd544e2bf
Source dataset
uspto-grants-2001_06
Patent number
US06251921B1

Reaction notes

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