Methanesulfonyl chloride → (2R)-4-(1,2-Dihydro-5-acenaphthylenyl)-1-{2-[(1S)-6-(1,1-dioxido-2-isothiazolidinyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl}-2-methylpiperazine

HRID 2056771Notes

Reaction equation

HRID 2056771 reaction equation
[O:1]=[S:2]1(=[O:20])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[CH:9][C:10]2[C@H:15]([CH2:16][CH2:17]O)[O:14][CH2:13][CH2:12][C:11]=2[CH:19]=1.CS(Cl)(=O)=O.CS(OCC[C@H]1C2C=CC(C(N)=O)=CC=2CCO1)(=O)=O.S([O-])(=O)(=O)C.[CH2:51]1[C:61]2=[C:62]3[C:57](=[CH:58][CH:59]=[CH:60]2)[C:56]([N:63]2[CH2:68][CH2:67][NH:66][C@H:65]([CH3:69])[CH2:64]2)=[CH:55][CH:54]=[C:53]3[CH2:52]1>>[CH2:51]1[C:61]2=[C:62]3[C:57](=[CH:58][CH:59]=[CH:60]2)[C:56]([N:63]2[CH2:68][CH2:67][N:66]([CH2:17][CH2:16][C@H:15]4[C:10]5[CH:9]=[CH:8][C:7]([N:3]6[CH2:4][CH2:5][CH2:6][S:2]6(=[O:20])=[O:1])=[CH:19][C:11]=5[CH2:12][CH2:13][O:14]4)[C@H:65]([CH3:69])[CH2:64]2)=[CH:55][CH:54]=[C:53]3[CH2:52]1

Participants

6

Reactant 5

HCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 69307361(3R)-1-(1,2-Dihydro-5-acenaphthylenyl)-3-methylpiperazineHCID 693078202-[(1S)-6-(1,1-Dioxido-2-isothiazolidinyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanolHCID 865960122-[(1S)-6-(aminocarbonyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl methanesulfonate

Product 1

HCID 69310596(2R)-4-(1,2-Dihydro-5-acenaphthylenyl)-1-{2-[(1S)-6-(1,1-dioxido-2-isothiazolidinyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl}-2-methylpiperazine

Procedure

2-[(1S)-6-(1,1-Dioxido-2-isothiazolidinyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanol was reacted with methanesulfonyl chloride, as described for the preparation of 2-[(1S)-6-(aminocarbonyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl methanesulfonate. The resultant crude mesylate was then condensed with (3R)-1-(1,2-dihydro-5-acenaphthylenyl)-3-methylpiperazine, as described for Example 1b), to yield the title compound. M+H=532.

Sources & evidence

ORD record
ord-05cfc575a8394366ab8cc5b698f60753
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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