Triethylamine → 2-(5-Methoxy-6-methylpyridin-3-yl)-4-(2,4,6-trifluorobenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772982Notes

Reaction equation

HRID 1772982 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][NH2:5].C([N:15](CC)C(C)C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.ClC1C=C(F)C(CN2[C:51]3[N:52]=[CH:53][CH:54]=[CH:55][C:50]=3[S:49](=[O:57])(=[O:56])[N:48]([C:58]3[CH:63]=[CH:62][C:61](OC)=[C:60]([O:66][CH3:67])[CH:59]=3)[C:47]2=[O:68])=C(F)C=1>>[CH3:67][O:66][C:60]1[CH:59]=[C:58]([N:48]2[C:47](=[O:68])[N:5]([CH2:4][C:3]3[C:2]([F:1])=[CH:9][C:8]([F:10])=[CH:7][C:6]=3[F:11])[C:51]3[N:52]=[CH:53][CH:54]=[CH:55][C:50]=3[S:49]2(=[O:56])=[O:57])[CH:63]=[N:15][C:61]=1[CH3:62]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27770462,4,6-TrifluorobenzylamineHCID 727219834-(4-Chloro-2,6-difluorobenzyl)-2-(3,4-dimethoxyphenyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727208772-(5-Methoxy-6-methylpyridin-3-yl)-4-(2,4,6-trifluorobenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Procedure

The title compound (52 mg, 0.11 mmol) was prepared in two steps from (IntC14) (88 mg, 0.28 mmol), 2,4,6-trifluorobenzyl amine (58 mg, 0.36 mmol) and N,N-diisopropylethylamine (100 uL, 0.57 mmol); followed by 1,1′-carbonyldiimidazole (110 mg, 0.68 mmol) and triethylamine (45 uL, 0.32 mmol) using the methods of (97).

Sources & evidence

ORD record
ord-86ecd0d13d2d4521aa793a8497942b33
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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