Trifluoroacetic acid → 4-(2,6-Difluoro-4-methoxybenzyl)-2-[6-methoxy-5-(methylamino)pyridin-3-yl]-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772983Notes

Reaction equation

HRID 1772983 reaction equation
C(OC(=O)NC[C:9]1[C:10]([O:26][CH3:27])=[N:11][CH:12]=[C:13]([NH:15][S:16]([C:19]2[C:20](Cl)=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:14]=1)(C)(C)C.[F:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[C:34]([F:40])[C:31]=1[CH2:32][NH2:33].C([N:44]([CH2:48]C)C(C)C)(C)C.[C:50](N1C=CN=C1)(N1C=CN=C1)=[O:51].C(N(CC)CC)C.FC1C=C(OC)C=C(F)C=1CN1C2N=CC=CC=2S(=O)(=O)N(C2C=CC(OC)=C(OC)C=2)C1=O.C(O)(C(F)(F)F)=O.FC1C=C(OC)C=C(F)C=1CN1C2C=CC=CC=2S(=O)(=O)N(C2C=CC(OC)=C(NC)N=2)C1=O>CC#N.C(Cl)Cl>[F:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[C:34]([F:40])[C:31]=1[CH2:32][N:33]1[C:20]2[N:21]=[CH:22][CH:23]=[CH:24][C:19]=2[S:16](=[O:17])(=[O:18])[N:15]([C:13]2[CH:12]=[N:11][C:10]([O:26][CH3:27])=[C:9]([NH:44][CH3:48])[CH:14]=2)[C:50]1=[O:51]

Participants

11

Reactant 8

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 38660872,6-Difluoro-4-methoxybenzylamineHCID 727208804-(2,6-Difluoro-4-methoxybenzyl)-2-[5-methoxy-6-(methylamino)pyridin-2-yl]-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideHCID 900546714-(2,6-difluoro-4-methoxybenzyl)-2-(3,4-dimethoxyphenyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3 (4H)-one 1,1-dioxideHCID 131734699tert-Butyl (5-{[(2-chloropyridin-3-yl)sulfonyl]amino}-2-methoxypyridin-3-yl)methylcarbamate

Product 1

HCID 727209824-(2,6-Difluoro-4-methoxybenzyl)-2-[6-methoxy-5-(methylamino)pyridin-3-yl]-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 64%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound (155 mg, 0.32 mmol) was prepared in three steps from tert-butyl(5-{[(2-chloropyridin-3-yl)sulfonyl]amino}-2-methoxypyridin-3-yl)methylcarbamate (IntC15) (214 mg, 0.5 mmol), 2,6-difluoro-4-methoxybenzylamine (0.28 mL, 2.0 mmol) and N,N-diisopropylethylamine (0.18 mL, 1.0 mmol) in MeCN (3 mL) at 120° C. for 6 hours; followed by 1,1′-carbonyldiimidazole (350 mg, 2.16 mmol) and triethylamine (0.15 mL, 1.08 mmol) using the methods of (95); followed by TFA (2 mL) in DCM (3 mL) at rt using the method of (179), step 2.

Sources & evidence

ORD record
ord-b7b065399aef4966931617ce7c827bb0
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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