2-Tolyl isocyanate → 1-{2-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-4-fluoro-phenyl}-3-o-tolyl-urea

HRID 2211874Notes

Reaction equation

HRID 2211874 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[NH2:25])[CH2:12][CH2:11]2)=[N:2]1.[C:26]1([CH3:35])[C:27]([N:32]=[C:33]=[O:34])=[CH:28][CH:29]=[CH:30][CH:31]=1>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[NH:25][C:33]([NH:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH3:35])=[O:34])[CH2:12][CH2:11]2)=[N:2]1

Participants

3

Reactant 2

HCID 691942-Tolyl isocyanateHCID 219632182-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-4-fluoro-phenylamine

Product 1

HCID 219635011-{2-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-4-fluoro-phenyl}-3-o-tolyl-ureaYield 71.5%

Procedure

Starting from 2-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-4-fluoro-phenylamine (142 mg, 0.4 mmol) and 2-tolyl isocyanate (57 μL, 0.4 mmol) and following the procedure as outlined in Example 60, 140 mg of 1-{2-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-4-fluoro-phenyl}-3-o-tolyl-urea was isolated as an off white powder in 98% purity @ 214 nm; LCMS (APCI): 490 [M+H]+.

Sources & evidence

ORD record
ord-8a79461aabf147e29eafb7c00f2de93f
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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