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

HRID 1772966Notes

Reaction equation

HRID 1772966 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([F:32])[C:3]=1[CH2:4][NH:5][C:6]1[C:11]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34].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>>[F:1][C:2]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([F:32])[C:3]=1[CH2:4][N:5]1[C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:11]=2[S:12](=[O:13])(=[O:14])[N:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[C:33]1=[O:34]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 900227412-[(2,6-difluoro-4-methoxybenzyl)amino]-N-(3,4-dimethoxyphenyl)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 900546714-(2,6-difluoro-4-methoxybenzyl)-2-(3,4-dimethoxyphenyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3 (4H)-one 1,1-dioxideYield 41.9%

Procedure

The title compound (89 mg, 0.18 mmol) was prepared from 2-[(2,6-difluoro-4-methoxybenzyl)amino]-N-(3,4-dimethoxyphenyl)pyridine-3-sulfonamide (198 mg, 0.43 mmol), 1,1′-carbonyldiimidazole (279 mg, 1.72 mmol) and triethylamine (0.12 mL, 0.86 mmol) using the methods of (132).

Sources & evidence

ORD record
ord-c483489441aa4dfba35895ed8725e172
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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