Dichloromethane → HCID 66711343, compound
Reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([CH2:12][NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:5]2[N:4]=1.C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:31])C=1>>[CH3:1][S:2]([C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([CH2:12][NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:5]2[N:4]=1)=[O:31]Participants
Procedure
(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-ylmethyl)-phenyl-amine (0.280 g, 1.04 mmol) was dissolved in Methylene chloride (5 mL, 80 mmol) and the solution was treated with m-Chloroperbenzoic acid (0.313 g, 1.40 mmol) at room temperature. The reaction was allowed to stir until HPLC showed consumption of starting materials. The reaction mixture was poured over saturated sodium bicarbonate and organics were extracted with dichloromethane. Combined extracts were then dried over sodium sulfate, filtered and reduced. The crude reaction mixture was purified by Isco flash column chromatography (hexanes/ethyl acetate eluent) and combined fractions were reduced and dried under vacuum to afford 83 mg of (2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-ylmethyl)-phenyl-amine. (M+H)=287.0. 1H NMR (400 MHz, DMSO, d6) δ 9.24 (s, 1H), 7.25 (m, 1H), 7.10 (m, 3H), 6.64 (d, 2H, J=8.08 Hz), 6.55 (t, 1H, J=7.12 Hz), 6.22 (m, 1H), 4.68 (m, 2H), 2.92 (s, 3H).
Workup
- customconsumption of starting materials
- additionThe reaction mixture was poured over saturated sodium bicarbonate
- extractionorganics were extracted with dichloromethane
- dry with materialCombined extracts were then dried over sodium sulfate
- filtrationfiltered
- customThe crude reaction mixture
- customwas purified by Isco flash column chromatography (hexanes/ethyl acetate eluent)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-40c289b0dcb54a55989a803e0c450a48
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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