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

HRID 1772979Notes

Reaction equation

HRID 1772979 reaction equation
Cl[C:2]1[C:7]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][CH3:20])[N:13]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.FC1C=C(OC)C=C(F)C=1CN.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[F:52][C:53]1[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[C:79]([F:85])[C:54]=1[CH2:55][N:56]1C2N=CC=CC=2S(=O)(=O)N(C2C=CC(OC)=C(OC)C=2)[C:57]1=[O:78]>>[F:52][C:53]1[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[C:79]([F:85])[C:54]=1[CH2:55][N:56]1[C:2]2[N:3]=[CH:4][CH:5]=[CH:6][C:7]=2[S:8](=[O:10])(=[O:9])[N:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][CH3:20])[N:13]=2)[C:57]1=[O:78]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 38660872,6-Difluoro-4-methoxybenzylamineHCID 900297582-Chloro-N-(6-methoxy-5-methylpyridin-2-yl)pyridine-3-sulfonamideHCID 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 727208784-(2,6-Difluoro-4-methoxybenzyl)-2-(6-methoxy-5-methylpyridin-2-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Procedure

The title compound (110 mg, 0.23 mmol) was prepared in two steps from 2-chloro-N-(6-methoxy-5-methylpyridin-2-yl)pyridine-3-sulfonamide (IntC11) (320 mg, 1.02 mmol) and 2,6-difluoro-4-methoxybenzylamine (212 mg, 1.22 mmol); followed by 1,1′-carbonyldiimidazole (403 mg, 2.49 mmol) and triethylamine (173 uL, 1.24 mmol) using the methods of (95).

Sources & evidence

ORD record
ord-b6d5182c94db4a47b64a7e9c87102146
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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