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

HRID 1772978Notes

Reaction equation

HRID 1772978 reaction equation
C(OC(=O)NC[C:9]1[C:10]([O:26][CH3:27])=[N:11][C:12]([NH:15][S:16]([C:19]2[C:20](Cl)=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])=[CH:13][CH:14]=1)(C)(C)C.[F:29][C:30]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[C:31]=1[CH2:32][NH2:33].C([N:43]([CH2:47]C)C(C)C)(C)C.[C:49](N1C=CN=C1)(N1C=CN=C1)=[O:50].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>[CH3:27][O:26][C:10]1[N:11]=[C:12]([N:15]2[C:49](=[O:50])[N:33]([CH2:32][C:31]3[C:30]([F:29])=[CH:37][C:36]([F:38])=[CH:35][C:34]=3[F:39])[C:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]=3[S:16]2(=[O:17])=[O:18])[CH:13]=[CH:14][C:9]=1[NH:43][CH3:47]

Participants

11

Reactant 8

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27770462,4,6-TrifluorobenzylamineHCID 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 131734696tert-Butyl (6-{[(2-chloropyridin-3-yl)sulfonyl]amino}-2-methoxypyridin-3-yl)methylcarbamate

Product 1

HCID 727207782-[6-Methoxy-5-(methylamino)pyridin-2-yl]-4-(2,4,6-trifluorobenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 31.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound (266 mg, 0.55 mmol) was prepared in three steps from tert-butyl(6-{[(2-chloropyridin-3-yl)sulfonyl]amino}-2-methoxypyridin-3-yl)methylcarbamate (IntC8) (755 mg, 1.76 mmol), 2,4,6-trifluorobenzylamine (1.13 g, 7.01 mmol) and N,N-diisopropylethylamine (0.46 mL, 2.64 mmol) in MeCN (10 mL) at 120° C. for 12 hours; followed by 1,1′-carbonyldiimidazole (832 mg, 5.13 mmol) and triethylamine (358 uL, 2.57 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-8de1416011574adcb19e8b5b6c87ad45
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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