Triphenylphosphine → 4-(2-Chloro-4,6-difluorobenzyl)-2-(2,6-dimethoxypyridin-4-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772996Notes

Reaction equation

HRID 1772996 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[C:14](=[O:15])[NH:13][C:12]3[N:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10]2(=[O:21])=[O:20])[CH:6]=[C:5]([O:22][CH3:23])[N:4]=1.[Cl:24][C:25]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[C:26]=1[CH2:27]O.CN(C(/N=N/C(N(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COC1C=C(N2C(=O)N(CC3C(C)=CC(F)=CN=3)C3C=CC=CC=3S2(=O)=O)C=C(OC)N=1>C(Cl)Cl>[Cl:24][C:25]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[C:26]=1[CH2:27][N:13]1[C:12]2[N:16]=[CH:17][CH:18]=[CH:19][C:11]=2[S:10](=[O:21])(=[O:20])[N:9]([C:7]2[CH:6]=[C:5]([O:22][CH3:23])[N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[C:14]1=[O:15]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 5353800DiamideHCID 727211812-(2,6-Dimethoxypyridin-4-yl)-4-[(5-fluoro-3-methylpyridin-2-yl)methyl]-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideHCID 90022378(2-Chloro-4,6-difluorophenyl)methanolHCID 900547912-(2,6-Dimethoxypyridin-4-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727208814-(2-Chloro-4,6-difluorobenzyl)-2-(2,6-dimethoxypyridin-4-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (74 mg, 0.15 mmol) was prepared from 2-(2,6-dimethoxypyridin-4-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide (IntF3) (101 mg, 0.30 mmol), 2-chloro-4,6-difluorobenzyl alcohol (IntA22) (59 mg, 0.33 mmol), TMAD (57 mg, 0.33 mmol) and triphenyl phosphine (86 mg, 0.33 mmol) in DCM (3 mL) using the methods of (162).

Sources & evidence

ORD record
ord-c640d0d191d94c22a870d4edf46e5020
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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