4-(Difluoromethoxy)aniline → 2-[(6-Aminopyridin-3-yl)methyl]-4-{[4-(difluoromethoxy)phenyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729321Notes

Reaction equation

HRID 729321 reaction equation
[F:1][CH:2]([F:40])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12](=[O:39])[N:13]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([NH:31]C(=O)OC(C)(C)C)=[N:29][CH:30]=3)[S:14](=[O:23])(=[O:22])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:5]=1.FC(F)OC1C=CC(N)=CC=1>>[NH2:31][C:28]1[N:29]=[CH:30][C:25]([CH2:24][N:13]2[C:12](=[O:39])[C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:40])[F:1])=[CH:9][CH:8]=3)=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:14]2(=[O:22])=[O:23])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 7373634-(Difluoromethoxy)anilineHCID 86623729tert-Butyl (5-{[4-{[4-(difluoromethoxy)phenyl]amino}-1,1-dioxido-3-oxo-5-phenylisothiazol-2(3H)-yl]methyl}pyridin-2-yl)carbamate

Product 1

HCID 115111802-[(6-Aminopyridin-3-yl)methyl]-4-{[4-(difluoromethoxy)phenyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Procedure

The title compound was prepared from tert-butyl (5-{[4-{[4-(difluoromethoxy)phenyl]amino}-1,1-dioxido-3-oxo-5-phenylisothiazol-2(3H)-yl]methyl}pyridin-2-yl)carbamate and 4-(difluoromethoxy)aniline in a similar manner as described for e.g. Example 5. 1H NMR (400 MHz, DMSO): δ 3.57-3.71 (m, 2H), 5.77 (s, 2H), 6.15 (d, 1H), 6.91 (d, 1H), 7.23-7.28 (m, 2H), 7.38-7.48 (m, 6H), 7.86 (d, 1H); Mass Spectrum: M+H+ 473.

Sources & evidence

ORD record
ord-99f3bdb14a6847edb113e90ad469fc4e
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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