Methanesulfonyl chloride → 5-[(3R)-3-Methyl-4-(2-{(1S)-6-[(2-oxo-1,3-oxazolidin-3-yl)methyl]-3,4-dihydro-1H-2-benzopyran-1-yl}ethyl)piperazinyl]-2-naphthonitrile

HRID 2056762Notes

Reaction equation

HRID 2056762 reaction equation
O[CH2:2][CH2:3][C@H:4]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][N:15]3[CH2:19][CH2:18][O:17][C:16]3=[O:20])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5]1.CS(Cl)(=O)=O.CS(OCC[C@H]1C2C=CC(C(N)=O)=CC=2CCO1)(=O)=O.S([O-])(=O)(=O)C.[C:51]([C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][CH:62]=1)[C:59]([N:63]1[CH2:68][CH2:67][NH:66][C@H:65]([CH3:69])[CH2:64]1)=[CH:58][CH:57]=[CH:56]2)#[N:52]>>[CH3:69][C@H:65]1[N:66]([CH2:2][CH2:3][C@H:4]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14][N:15]4[CH2:19][CH2:18][O:17][C:16]4=[O:20])=[CH:13][C:8]=3[CH2:7][CH2:6][O:5]2)[CH2:67][CH2:68][N:63]([C:59]2[CH:58]=[CH:57][CH:56]=[C:55]3[C:60]=2[CH:61]=[CH:62][C:53]([C:51]#[N:52])=[CH:54]3)[CH2:64]1

Participants

6

Reactant 5

HCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 693084103-{[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-oneHCID 69308435(3R)-1-(6-cyano-1-naphthyl)-3-methylpiperazineHCID 865960122-[(1S)-6-(aminocarbonyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl methanesulfonate

Product 1

HCID 693101355-[(3R)-3-Methyl-4-(2-{(1S)-6-[(2-oxo-1,3-oxazolidin-3-yl)methyl]-3,4-dihydro-1H-2-benzopyran-1-yl}ethyl)piperazinyl]-2-naphthonitrile

Procedure

3-{[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one 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-(6-cyano-1-naphthyl)-3-methylpiperazine, as described for Example 1b), to yield the title compound. M+H=511.

Sources & evidence

ORD record
ord-4d6b3441723745159718f55ada54344e
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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