1,1'-Carbonyldiimidazole → 4-(4-Chloro-2,6-difluorobenzyl)-2-(3,4-dimethoxyphenyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772968Notes

Reaction equation

HRID 1772968 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][NH2:5].C(N(CC)C(C)C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O.FC1C=C(OC)C=C(F)C=1CN1[C:42]2[N:43]=[CH:44][CH:45]=[CH:46][C:41]=2[S:40](=[O:48])(=[O:47])[N:39]([C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[C:51]([O:57][CH3:58])[CH:50]=2)[C:38]1=[O:59]>CN(C=O)C>[Cl:10][C:8]1[CH:9]=[C:2]([F:1])[C:3]([CH2:4][N:5]2[C:42]3[N:43]=[CH:44][CH:45]=[CH:46][C:41]=3[S:40](=[O:48])(=[O:47])[N:39]([C:49]3[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[C:51]([O:57][CH3:58])[CH:50]=3)[C:38]2=[O:59])=[C:6]([F:11])[CH:7]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 17750831(4-Chloro-2,6-difluorophenyl)methanamineHCID 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 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound (38 mg, 0.08 mmol) was prepared in two steps from (IntC1) (208 mg, 0.63 mmol), 2,6-difluoro-4-chlorobenzylamine (135 mg, 0.76 mmol) and N,N-diisopropylethylamine (113 uL, 0.63 mmol); followed by 1,1′-carbonyldiimidazole (166 mg, 1.0 mmol) in DMF (8.5 mL) using the methods of (95).

Sources & evidence

ORD record
ord-6215cde54ef94218819ecabf3e7414d4
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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