Piperidine → 3-(Naphthalen-2-yl-sulfonylamino)-N-(1-methyl-2,2-dioxo-7-piperidin-1-ylmethyl-1,2,3,4-tetrahydro-2lambda6-benzo[c][1,2]thiazin-4-yl)-3-phenyl-propionamide

HRID 32088Notes

Reaction equation

O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:11]([NH:12][C:13](=[O:36])[CH2:14][CH:15]([NH:22][S:23]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)(=[O:25])=[O:24])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][S:9](=[O:38])(=[O:37])[N:8]([CH3:39])[C:7]=2[CH:40]=1.S([O-])(=O)(=O)C.[NH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>>[CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[S:23]([NH:22][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:14][C:13]([NH:12][CH:11]1[CH2:10][S:9](=[O:37])(=[O:38])[N:8]([CH3:39])[C:7]2[CH:40]=[C:3]([CH2:2][N:46]3[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]3)[CH:4]=[CH:5][C:6]1=2)=[O:36])(=[O:25])=[O:24]

Participants

Reactant 3

HCID 8082Piperidine

HCID 85257Methanesulfonate

HCID 68926983HCID 68926983, compound

Product 1

HCID 689286533-(Naphthalen-2-yl-sulfonylamino)-N-(1-methyl-2,2-dioxo-7-piperidin-1-ylmethyl-1,2,3,4-tetrahydro-2lambda6-benzo[c][1,2]thiazin-4-yl)-3-phenyl-propionamide

Procedure

The title compound was prepared from N-(7-hydroxymethyl-1-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2λ6-benzo[c][1,2]thiazin-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide (Example 12, Step D) via its mesylate and addition of piperidine by a method similar to that described in Example 12, Step E. MS (+ESI, m/z): 647 (M+H)+.

Sources & evidence

ORD record: ord-e712505069774998bf9341b5d9f346b9
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425631B2

Reaction notes

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