Dimethylformamide → 2-(3,5-Dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772977Notes

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(CC)[CH:16]([CH3:18])[CH3:17])(C)C.[C:21]([N:28]1[CH:32]=[CH:31]N=C1)(N1C=CN=C1)=[O:22].C(N([CH2:38][CH3:39])CC)C.FC1C=C(OC)C=C(F)C=1CN1[C:49]2[N:50]=[CH:51][CH:52]=[CH:53][C:48]=2[S:47](=[O:55])(=[O:54])N(C2C=CC(OC)=C(OC)C=2)C1=O.[CH3:74]N(C=O)C>>[CH3:74][C:38]1[CH:39]=[C:32]([N:28]2[C:21](=[O:22])[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:49]3[N:50]=[CH:51][CH:52]=[CH:53][C:48]=3[S:47]2(=[O:55])=[O:54])[CH:31]=[C:16]([CH3:17])[CH:18]=1

Participants

Reactant 6

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 682631,1'-Carbonyldiimidazole

HCID 81531Diisopropylethylamine

HCID 27770462,4,6-Trifluorobenzylamine

HCID 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 727218922-(3,5-Dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Procedure

The title compound (89 mg, 0.20 mmol) was prepared in two steps from (IntC6) (209 mg, 0.71 mmol), 2,4,6-trifluorobenzylamine (107 uL, 0.88 mmol) and N,N-diisopropylethylamine (252 uL, 1.41 mmol); followed by 1,1′-carbonyldiimidazole (386 mg, 2.38 mmol) and triethylamine (114 uL, 0.82 mmol) in DMF (9.5 mL) using the methods of (95).

Sources & evidence

ORD record: ord-d9761fc55c944257babd43b0c7b38a67
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249160B2

Reaction notes

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