m-Chloroperbenzoic acid → Hydrochloric Acid
Reaction equation
CS[C:3]1[N:4]=[N:5][C:6]([C:24]([NH2:26])=[O:25])=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:17])=[CH:12][CH:11]=2)[N:8]=1.C1C=C([Cl:33])C=C(C(OO)=O)C=1.CCN(C(C)C)C(C)C.[NH:47]1[CH2:52][CH2:51][CH2:50][C@@H:49]([O:53][C:54]2[C:63]3[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH:57]=[CH:56][N:55]=2)[CH2:48]1>CN1C(=O)CCC1.CCOC(C)=O>[C:54]1([O:53][C@@H:49]2[CH2:50][CH2:51][CH2:52][N:47]([C:3]3[N:4]=[N:5][C:6]([C:24]([NH2:26])=[O:25])=[C:7]([NH:9][C:10]4[CH:15]=[CH:14][C:13]([C:16]([N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[O:17])=[CH:12][CH:11]=4)[N:8]=3)[CH2:48]2)[C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH:57]=[CH:56][N:55]=1.[ClH:33]Participants
Reactant 4
Product 2
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-(methylthio)-5-(4-(morpholine-4-carbonyl)phenylamino)-1,2,4-triazine-6-carboxamide (75 mg, 0.20 mmol) in NMP (4 mL) was added mCPBA (77% strength, 140 mg, 0.60 mmol). The mixture was stirred at RT for 30 m to yield a mixture of corresponding sulfone and sulfoxide. To the mixture was then added DIEA (0.28 mL, 1.60 mmol) and Compound 54 (100 mg, 0.40 mmol). The mixture was heated at 90° C. for 90 min. The mixture was cooled, diluted with EtOAc (100 mL), washed with 1N NaOH and brine, dried, and concentrated in vacuo. The residue was subjected to flash column chromatography with 50 to 100% EtOAc in DCM and further subjected to reverse phase preparative HPLC to afford the title compound (55) as an HCl salt (45 mg). MS found for C29H30N8O4 as (M+H)+ 555.2, (M−H)− 553.3. UV: λ=275 nm.
Workup
- customto yield
- temperatureThe mixture was heated at 90° C. for 90 min
- temperatureThe mixture was cooled
- washwashed with 1N NaOH and brine
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4e694af81d9f47e29f10aecaee462ce0
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382246B2
Reaction notes
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