3-(Bromomethyl)pyridine → 5-Phenyl-4-[(4-phenylbutyl)amino]-2-(pyridin-3-ylmethyl)isothiazol-3(2H)-one 1,1-dioxide

HRID 2422055Notes

Reaction equation

HRID 2422055 reaction equation
C([N:5]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:6]1(=[O:29])=[O:28])(C)(C)C.Br[CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>>[C:22]1([C:7]2[S:6](=[O:28])(=[O:29])[N:5]([CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[C:9](=[O:10])[C:8]=2[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 2459343-(Bromomethyl)pyridineHCID 114952832-tert-Butyl-5-phenyl-4-[(4-phenylbutyl)amino]isothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 117120235-Phenyl-4-[(4-phenylbutyl)amino]-2-(pyridin-3-ylmethyl)isothiazol-3(2H)-one 1,1-dioxide

Procedure

The title compound was prepared from 2-tert-butyl-5-phenyl-4-[(4-phenylbutyl)amino]isothiazol-3(2H)-one 1,1-dioxide (Example 1) and 3-(bromomethyl)pyridine in a similar manner as described for e.g. Example 2 and 3 1H NMR (500 MHz, CDCl3): δ 8.80-8.76 (m, 1H), 8.62-8.58 (m, 1H), 7.89-7.85 (m, 1H), 7.53-7.41 (m, 5H), 7.34-7.24 (m, 3H), 7.22-7.17 (m, 1H), 7.09-7.04 (m, 2H), 5.31-5.25 (m, 1H), 4.84 (s, 2H), 2.90-2.83 (m, 2H), 2.49-2.42 (m, 2H), 1.44-1.35 (m, 4H); 13C NMR (125 MHz, CDCl3): δ 159.1, 150.3, 149.8, 141.6, 136.7, 135.5, 131.7, 130.3, 130.0, 128.8, 128.5, 128.4, 126.1, 124.7, 123.7, 107.0, 44.1, 41.1, 35.3, 29.0, 28.2; Mass Spectrum: M−H+ 448.

Sources & evidence

ORD record
ord-648ad87655474a07a6f3b9565ccc6952
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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