Water → HCID 21182943, compound

HRID 377406Notes

Reaction equation

[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

Participants

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

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

Sources & evidence

ORD record: ord-2a53266674cf4a459283c908c2ca02c2
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06025382

Reaction notes

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