Trifluoroacetic acid → 4-(2,6-Difluoro-4-methoxybenzyl)-2-[6-methoxy-5-(methylamino)pyridin-3-yl]-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide
Reaction equation
C(OC(=O)NC[C:9]1[C:10]([O:28][CH3:29])=[N:11][CH:12]=[C:13]([N:15]2[C:20](=[O:21])[NH:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[S:16]2(=[O:27])=[O:26])[CH:14]=1)(C)(C)C.[F:31][C:32]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[C:36]([F:42])[C:33]=1[CH2:34]Br.C([O-])([O-])=O.[K+].[K+].C(O)(C(F)(F)F)=O.FC1C=C(OC)C=C(F)C=1[CH2:59][N:60]1C2C=CC=CC=2S(=O)(=O)N(C2C=CC(OC)=C(NC)N=2)C1=O>CN(C=O)C.C(Cl)Cl>[F:31][C:32]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[C:36]([F:42])[C:33]=1[CH2:34][N:19]1[C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16](=[O:27])(=[O:26])[N:15]([C:13]2[CH:12]=[N:11][C:10]([O:28][CH3:29])=[C:9]([NH:60][CH3:59])[CH:14]=2)[C:20]1=[O:21]Participants
8
Reactant 5
HCID 6422Trifluoroacetic acid
HCID 11430Potassium Carbonate
HCID 33542722,6-Difluoro-4-methoxybenzyl bromide
HCID 727208804-(2,6-Difluoro-4-methoxybenzyl)-2-[5-methoxy-6-(methylamino)pyridin-2-yl]-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide
HCID 131734693tert-Butyl [5-(1,1-dioxido-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazin-2-yl)-2-methoxypyridin-3-yl]methylcarbamateProduct 1
Reagents, catalysts & solvents 2
Procedure
The title compound (120 mg, 0.24 mmol) was prepared in two steps from tert-butyl[5-(1,1-dioxido-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazin-2-yl)-2-methoxypyridin-3-yl]methylcarbamate (IntA35) (130 mg, 0.3 mmol), 2,6-difluoro-4-methoxybenzyl bromide (85 mg, 0.36 mmol) and K2CO3 (124 mg, 0.9 mmol) in DMF (1.5 mL); followed by TFA (2 mL) in DCM (3 mL) at rt using the methods of (179).
Sources & evidence
- ORD record
- ord-cfe7c7486a3344ac93d904d52d927d1c
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249160B2
Reaction notes
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