m-Chloroperbenzoic acid → N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-methanesulfonamide

HRID 1262353Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19]([S:22][CH3:23])=[N:20]3)=[CH:15][CH:14]=2)=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>CN(C)C=O>[CH3:23][S:22]([C:19]1[N:18]=[CH:17][C:16]2=[CH:15][CH:14]=[C:13]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][C:6]=3[NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[N:21]2[N:20]=1)=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a RB flask, N-[5-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide (580 mg, 1.7 mmol) and N,N-Dimethylformamide (13 mL,) were added. Resulting solution was cooled to 0° C., m-CPBA (70:30, m-Chloroperbenzoic acid:3-Chlorobenzoic acid, 431 mg, 1.75 mmol) was added in portion over 10 minutes. After 2 h, solvent was removed .The residue was partitioned with DCM and sat. NaHCO3 solution. The organic phase was separated, washed with brine, and dried over Magnesium sulfate. N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-methanesulfonamide was obtained as a yellow solid (539 mg, 89%) which was taken to the next step without further purifications. LCMS (E/I+) 365 (M+H).

Workup

customsolvent was removed .The residue
customwas partitioned with DCM and sat. NaHCO3 solution
customThe organic phase was separated
washwashed with brine
dry with materialdried over Magnesium sulfate

Sources & evidence

ORD record: ord-c4c1b66d963c4364943ab32b96e71db4
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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