Triethylamine → 2-(5,6-Dimethoxypyridin-3-yl)-1,1-bis(oxidanylidene)-4-[[2,4,6-tris(fluoranyl)phenyl]methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one

HRID 1772971Notes

Reaction equation

HRID 1772971 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(N1C=CN=C1)([N:14]1C=CN=C1)=O.C(N(CC)CC)C.FC1C=C(OC)C=C(F)C=1CN1[C:40]2[N:41]=[CH:42][CH:43]=[CH:44][C:39]=2[S:38](=[O:46])(=[O:45])[N:37]([C:47]2[CH:52]=C[C:50]([O:53][CH3:54])=[C:49]([O:55][CH3:56])[CH:48]=2)[C:36]1=[O:57]>CN(C=O)C>[CH3:56][O:55][C:49]1[CH:48]=[C:47]([N:37]2[C:36](=[O:57])[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:40]3[N:41]=[CH:42][CH:43]=[CH:44][C:39]=3[S:38]2(=[O:45])=[O:46])[CH:52]=[N:14][C:50]=1[O:53][CH3:54]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27770462,4,6-TrifluorobenzylamineHCID 900546714-(2,6-difluoro-4-methoxybenzyl)-2-(3,4-dimethoxyphenyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3 (4H)-one 1,1-dioxide

Product 1

HCID 727071432-(5,6-Dimethoxypyridin-3-yl)-1,1-bis(oxidanylidene)-4-[[2,4,6-tris(fluoranyl)phenyl]methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound (159 mg, 0.33 mmol) was prepared in two steps from (IntC4) (165 mg, 0.5 mmol), 2,4,6-trifluorobenzylamine (0.18 mL, 1.5 mmol); followed by 1,1′-carbonyldiimidazole (311 mg, 1.92 mmol), triethylamine (0.13 mL, 0.96 mmol) in DMF (1.5 mL) using the methods of (95).

Sources & evidence

ORD record
ord-d0b1928e0946431bbff9ccf1ad9df137
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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