Nicotinoyl chloride → 1'-(Pyridin-3-ylcarbonyl)spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665294Notes

Reaction equation

HRID 1665294 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1>>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([N:1]2[CH2:2][CH2:3][C:4]3([O:11][C:10]4[C:12]5[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=4[S:8][CH2:7]3)=[CH:16][CH:15]=[CH:14][CH:13]=5)[CH2:5][CH2:6]2)=[O:29])[CH:24]=1

Participants

3

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 57661820Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576618871'-(Pyridin-3-ylcarbonyl)spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 59 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, nicotinoyl chloride and conditions outlined in procedure N. M.p.=218-220° C.; 300 MHz 1H NMR (CDCl3) δ 8.71 (brs, 2H), 8.08 (d, J=7.5 Hz, 1H), 7.77 (m, 3H), 7.53 (t, J=7.5 Hz, 1H), 7.40 (m, 1H), 4.62 (m, 1H), 3.78 (m, 1H), 3.42 (m 2H), 2.99 (s, 2H), 2.24 (s, 2H), 1.90 (m, 2H); LCMS: 407 [M+H].

Sources & evidence

ORD record
ord-b18a5d67bf914011a093472006c969e4
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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