Methanesulfonate → (1S)1-{2-[(2R)-4-(1,2-Dihydro-5-acenaphthylenyl)-2-methylpiperazinyl]ethyl}-1,3-dihydro-2-benzofuran-5-carboxamide

HRID 2056749Notes

Reaction equation

HRID 2056749 reaction equation
O[CH2:2][CH2:3][CH:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([NH2:15])=[O:14])=[CH:12][C:7]=2[CH2:6][O:5]1.CS([O-])(=O)=O.CS(OCC[C@H]1C2C=CC(C(N)=O)=CC=2CCO1)(=O)=O.[CH2:41]1[C:51]2=[C:52]3[C:47](=[CH:48][CH:49]=[CH:50]2)[C:46]([N:53]2[CH2:58][CH2:57][NH:56][C@H:55]([CH3:59])[CH2:54]2)=[CH:45][CH:44]=[C:43]3[CH2:42]1>>[CH2:41]1[C:51]2=[C:52]3[C:47](=[CH:48][CH:49]=[CH:50]2)[C:46]([N:53]2[CH2:58][CH2:57][N:56]([CH2:2][CH2:3][C@H:4]4[C:8]5[CH:9]=[CH:10][C:11]([C:13]([NH2:15])=[O:14])=[CH:12][C:7]=5[CH2:6][O:5]4)[C@H:55]([CH3:59])[CH2:54]2)=[CH:45][CH:44]=[C:43]3[CH2:42]1

Participants

5

Reactant 4

HCID 85257MethanesulfonateHCID 693072701-(2-Hydroxyethyl)-1,3-dihydro-2-benzofuran-5-carboxamideHCID 69307361(3R)-1-(1,2-Dihydro-5-acenaphthylenyl)-3-methylpiperazineHCID 865960122-[(1S)-6-(aminocarbonyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl methanesulfonate

Product 1

HCID 69308394(1S)1-{2-[(2R)-4-(1,2-Dihydro-5-acenaphthylenyl)-2-methylpiperazinyl]ethyl}-1,3-dihydro-2-benzofuran-5-carboxamide

Procedure

The title compound was prepared from 1-(2-hydroxyethyl)-1,3-dihydro-2-benzofuran-5-carboxamide by initial formation of the methanesulfonate as described for the preparation of 2-[(1S)-6-(aminocarbonyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl methanesulfonate, and condensation of this sulfonate with (3R)-1-(1,2-dihydro-5-acenaphthylenyl)-3-methylpiperazine, as described for Example 1b). The mixture of diastereomers was separated by chiral HPLC using a Chiracel OJ column, eluting with hexane/ethanol (1:1) with 0.2% dimethylethylamine. M+H=442.

Workup

  1. additionThe mixture of diastereomers
  2. customwas separated by chiral HPLC
  3. washeluting with hexane/ethanol (1:1) with 0.2% dimethylethylamine

Sources & evidence

ORD record
ord-d76ba4b8ec3f41499cc5bd6ceba8ae36
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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