3-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride → HCID 21963234, compound

HRID 2211925Notes

Reaction equation

HRID 2211925 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:15]([CH3:17])[CH3:16])=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[CH:10]=1)=[O:4].Cl.[N:19]1([C:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[S:27][N:26]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[S:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:25]([N:19]2[CH2:20][CH2:21][N:22]([CH2:2][C:3]([C:5]3[CH:6]=[CH:7][C:8]([CH:15]([CH3:17])[CH3:16])=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[CH:10]=3)=[O:4])[CH2:23][CH2:24]2)=[N:26]1

Participants

3

Reactant 2

HCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21963167HCID 21963167, compound

Product 1

HCID 21963234HCID 21963234, compoundYield 56%

Procedure

Starting with N-[5-(2-chloro-acetyl)-2-isopropyl-phenyl]-acetamide (0.50 g, 1.971 mmol), and 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.504 g, 1.971 mmol) and following the procedure as outlined in Example 517, N-{5-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-acetyl]-2-isopropyl-phenyl}-acetamide (0.480 g, 1.099 mmol) was obtained as its hydrochloride salt from treatment with dioxane/HCl(gas). Yield=56%. 100% purity at 254 nM. 1H NMR (400 MHz, DMSO-d6) δ 10.46 (bs, 1H), 9.63 (s, 1H), 8.12 (d, J=8.13 Hz, 1H), 8.09 (d, J=8.13 Hz, 1H), 7.90 (s, 1H), 7.79 (d, J=8.13 Hz, 1H), 7.61–7.52 (m, 2H), 7.45 (t, J=7.47 Hz, 1H), 5.13 (s, 2H), 4.12–4.01 (m, 2H), 3.67–3.49 (m, 8H), 3.40 (bs, H2O), 3.37–3.30 (m, 1H), 3.23 (heptet, J=6.81 Hz, 1H), 2.07 (s, 3H), 1.14 (d, J=6.81 Hz, 6H).

Sources & evidence

ORD record
ord-6cbe0c2a5b084e3f8b60a1e5b25290b6
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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