Triphosgene → 2-(1, 3-Benzothiazol-6-yl)-4-(2,6-difluoro-4-methoxybenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772981Notes

Reaction equation

HRID 1772981 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][S:11]([C:14]3[C:15](Cl)=[N:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.FC1C=C(OC)C=C(F)C=1CN.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[F:45][C:46]1[CH:75]=[C:74]([O:76][CH3:77])[CH:73]=[C:72]([F:78])[C:47]=1[CH2:48][N:49]1C2N=CC=CC=2S(=O)(=O)N(C2C=CC(OC)=C(OC)C=2)[C:50]1=[O:71].FC1C=CC2N(C(C3C=CC=CC=3F)C)C(=O)N(C3C=CC=C(SC)C=3)S(=O)(=O)C=2C=1>O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[C:50](=[O:71])[N:49]([CH2:48][C:47]4[C:72]([F:78])=[CH:73][C:74]([O:76][CH3:77])=[CH:75][C:46]=4[F:45])[C:15]4[N:16]=[CH:17][CH:18]=[CH:19][C:14]=4[S:11]3(=[O:13])=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 94429TriphosgeneHCID 38660872,6-Difluoro-4-methoxybenzylamineHCID 90030239N-(1,3-Benzothiazol-6-yl)-2-chloropyridine-3-sulfonamideHCID 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 900549197-Fluoro-4-[1-(2-fluorophenyl)ethyl]-2-[3-(methylsulfanyl)phenyl]-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727218942-(1, 3-Benzothiazol-6-yl)-4-(2,6-difluoro-4-methoxybenzyl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound (60 mg, 0.12 mmol) was prepared in two steps from N-(1,3-benzothiazol-6-yl)-2-chloropyridine-3-sulfonamide (IntC9) (300 mg, 0.92 mmol) and 2,6-difluoro-4-methoxybenzylamine (176 mg, 1.01 mmol) at 140° C. in a sealed tube; followed by triphosgene (288 mg, 0.97 mmol) in 1,4-dioxane (5 mL) at 110° C. for 16 h using the methods of (95) then (63).

Sources & evidence

ORD record
ord-6d2b594f660e4a98a2c5d8ee086fc1ba
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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