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

HRID 1772980Notes

Reaction equation

HRID 1772980 reaction equation
C(OC(=O)NC[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([NH:16][S:17]([C:20]2[C:21](Cl)=[N:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])=[CH:11][N:10]=1)(C)(C)C.[F:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([F:39])[C:30]=1[CH2:31][NH2:32].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>[F:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([F:39])[C:30]=1[CH2:31][N:32]1[C:21]2[N:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:17](=[O:18])(=[O:19])[N:16]([C:12]2[CH:11]=[N:10][C:9]([NH:43][CH3:47])=[C:14]([CH3:15])[CH:13]=2)[C:49]1=[O:50]

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 131734697tert-Butyl(5-{[(2-chloropyridin-3-yl)sulfonyl]amino}-3-methylpyridin-2-yl)methylcarbamate

Product 1

HCID 727209804-(2,6-Difluoro-4-methoxybenzyl)-2-[5-methyl-6-(methylamino)pyridin-3-yl]-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 26.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound (150 mg, 0.32 mmol) was prepared in three steps from tert-butyl(5-{[(2-chloropyridin-3-yl)sulfonyl]amino}-3-methylpyridin-2-yl)methylcarbamate (IntC13) (660 mg, 1.60 mmol), 2,6-difluoro-4-methoxybenzylamine (1.11 g, 6.41 mmol) and N,N-diisopropylethylamine (0.57 mL, 3.20 mmol) in MeCN (10 mL) at 120° C. for 12 hours; followed by 1,1′-carbonyldiimidazole (688 mg, 1.20 mmol) and triethylamine (296 uL, 2.12 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-3943b589797a455a88856cf1b944cdc2
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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