Thiomorpholine 1,1-dioxide → HCID 49838519, compound

HRID 472285Notes

Reaction equation

HRID 472285 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH:20]1[CH2:25][CH2:24][S:23](=[O:27])(=[O:26])[CH2:22][CH2:21]1>>[O:26]=[S:23]1(=[O:27])[CH2:24][CH2:25][N:20]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH:11][C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=4)[N:10]=3)[CH:5]=[CH:6][CH:7]=2)[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 6484228Thiomorpholine 1,1-dioxideHCID 67478829(8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(4-methoxy-phenyl)-amine

Product 1

HCID 49838519HCID 49838519, compound

Procedure

8-(1,1-dioxidothiomorpholin-4-yl)-N-(4-methoxyphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine was prepared from (8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(4-methoxy-phenyl)-amine (50.0 mg, 0.157 mmol) and thiomorpholine 1,1-dioxide (25.0 mg, 0.185 mmol) in a manner analogous to Example 30. Product isolated as a tan solid (0.052 g, 89%). MP=231-234° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.11 (dd, J=6.4, 1.1 Hz, 1H), 7.50-7.45 (m, 2H), 6.94-6.89 (m, 2H), 6.77 (dd, J=7.7, 6.7 Hz, 1H), 6.73 (dd, J=7.6, 0.9 Hz, 1H), 6.57 (s, 1H), 4.12-4.06 (m, 4H), 3.81 (s, 3H), 3.28-3.23 (m, 4H). MS=374 (MH)+.

Sources & evidence

ORD record
ord-6f6097983c2e4baa8c9167f2fe09cc00
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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