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

HRID 1772964Notes

Reaction equation

HRID 1772964 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([C:15]2[C:16]([NH:21][CH2:22][C:23]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[CH:25][C:24]=3[F:31])=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:32](N1C=CN=C1)(N1C=CN=C1)=[O:33].C(N(CC)CC)C.ClC1C=CC=C(F)C=1CN1C2C=CC=CC=2S(=O)(=O)N(C2C=CC(=O)N(C)C=2)C1=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[C:32](=[O:33])[N:21]([CH2:22][C:23]3[C:24]([F:31])=[CH:25][C:26]([F:30])=[CH:27][C:28]=3[F:29])[C:16]3[N:17]=[CH:18][CH:19]=[CH:20][C:15]=3[S:12]2(=[O:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90022973N-(3,4-dimethoxyphenyl)-2-[(2,4,6-trifluorobenzyl)amino]pyridine-3-sulfonamideHCID 900546724-(2-Chloro-6-fluorobenzyl)-2-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727219842-(3,4-dimethoxyphenyl)-4-(2,4,6-trifluorobenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 59.1%

Procedure

The title compound (63 mg, 0.13 mmol) was prepared from N-(3,4-dimethoxyphenyl)-2-[(2,4,6-trifluorobenzyl)amino]pyridine-3-sulfonamide (98 mg, 0.22 mmol), 1,1′-carbonyldiimidazole (143 mg, 0.88 mmol) and triethylamine (0.06 mL, 0.44 mmol) using the methods of (132).

Sources & evidence

ORD record
ord-b9f844df36e54a5b8042b21b534aae0e
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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