Dichloromethane → HCID 66711088, compound

HRID 1262023Notes

Reaction equation

HRID 1262023 reaction equation
[CH3:1][N:2]([C:7]1[C:12]([NH:13][C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20]([S:23][CH3:24])=[N:21]3)=[CH:16][CH:15]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:36])C=1.C(=O)(O)[O-].[Na+]>>[CH3:24][S:23]([C:20]1[N:19]=[CH:18][C:17]2=[CH:16][CH:15]=[C:14]([NH:13][C:12]3[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:4])=[O:5])=[N:8][CH:9]=[CH:10][CH:11]=3)[N:22]2[N:21]=1)=[O:36]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66712229HCID 66712229, compound

Product 1

HCID 66711088HCID 66711088, compoundYield 76.6%

Procedure

N-Methyl-N-[3-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-ylamino)-pyridin-2-yl]-methanesulfonamide (125.0 mg, 0.3430 mmol) was dissolved in Methylene chloride (5.00 mL, 78.0 mmol) and the solution was treated with m-Chloroperbenzoic acid (76.87 mg, 0.3430 mmol). The reaction was then allowed to stir overnight at room temperature. 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 100 mg of N-[3-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-ylamino)-pyridin-2-yl]-N-methyl-methanesulfonamide. 1H NMR (400 MHz, DMSO, d6) δ 9.11 (s, 1H), 8.24 (m, 1H), 8.07 (m, 1H), 7.46 (d, 1H, J=7.93 Hz), 7.33 (m, 1H), 7.26 (m, 1H), 7.14 (m, 1H), 3.23 (s, 3H), 3.18 (s, 3H), 2.89 (s, 3H).

Workup

  1. extractionorganics were extracted with dichloromethane
  2. dry with materialCombined extracts were then dried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude reaction mixture
  5. customwas purified by Isco flash column chromatography (hexanes/ethyl acetate eluent)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7a428ec7c1e44f2f9d4f3a935725fa49
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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