5-Amino-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide → N-(2,2-Dioxo-2,3-dihydro-1H-2lambda6-benzo[c]isothiazol-5-yl)-2-[4-(4-fluoro-benzyl)-piperidin-1-yl)-2-oxo-acetamide

HRID 2115004Notes

Reaction equation

HRID 2115004 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13](=[O:17])[C:14]([OH:16])=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]2[NH:28][S:27](=[O:30])(=[O:29])[CH2:26][C:25]=2[CH:31]=1>>[O:29]=[S:27]1(=[O:30])[CH2:26][C:25]2[CH:31]=[C:21]([NH:20][C:14](=[O:16])[C:13]([N:10]3[CH2:9][CH2:8][CH:7]([CH2:6][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)=[O:17])[CH:22]=[CH:23][C:24]=2[NH:28]1

Participants

3

Reactant 2

HCID 217951445-Amino-1,3-dihydrobenzo[c]isothiazole 2,2-dioxideHCID 51342220[4-(4-Fluorobenzyl)piperidin-1-yl](oxo)acetic acid

Product 1

HCID 69100356N-(2,2-Dioxo-2,3-dihydro-1H-2lambda6-benzo[c]isothiazol-5-yl)-2-[4-(4-fluoro-benzyl)-piperidin-1-yl)-2-oxo-acetamide

Procedure

The title compound is prepared from [4-(4-fluoro-benzyl) piperidin-1-yl]-oxo-acetic acid (Example 1a) and 5-amino-1,3-dihydro-2,1-benzisothiazole-2,2-dioxide according to the method described in Example 2. The filtered crystals are purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and toluene:methanol=4:1 as eluent. Melting Point: 183-184° C. (isopropanol)

Workup

  1. customThe filtered crystals are purified by column chromatography

Sources & evidence

ORD record
ord-cb6e1c1bcfe04ed4bfc9b6c3f70914f8
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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