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

HRID 1772984Notes

Reaction equation

HRID 1772984 reaction equation
C(OC(=O)NC[C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([NH:17][S:18]([C:21]2[C:22](Cl)=[N:23][CH:24]=[CH:25][CH:26]=2)(=[O:20])=[O:19])=[CH:11][N:10]=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>[CH3:16][O:15][C:14]1[CH:13]=[C:12]([N:17]2[C:50](=[O:51])[N:33]([CH2:32][C:31]3[C:30]([F:29])=[CH:37][C:36]([O:38][CH3:39])=[CH:35][C:34]=3[F:40])[C:22]3[N:23]=[CH:24][CH:25]=[CH:26][C:21]=3[S:18]2(=[O:19])=[O:20])[CH:11]=[N:10][C:9]=1[NH:44][CH3:48]

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 131734700tert-Butyl (5-{[(2-chloropyridin-3-yl)sulfonyl]amino}-3-methoxypyridin-2-yl)methylcarbamate

Product 1

HCID 727207812-[5-Methoxy-6-(methylamino)pyridin-3-yl]-4-(2,6-difluoro-4-methoxybenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 54%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound (133 mg, 0.27 mmol) was prepared in three steps from tert-butyl(5-{[(2-chloropyridin-3-yl)sulfonyl]amino}-3-methoxypyridin-2-yl)methylcarbamate (IntC17) (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 (259 mg, 1.6 mmol) and triethylamine (0.11 mL, 0.8 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-1909e197ec4a403aa64c86044b7db189
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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