m-Chloroperbenzoic acid → HCID 69309550, compound

HRID 1947033Notes

Reaction equation

HRID 1947033 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[C:16]1[CH:21]=[CH:20][N:19]=[C:18](SC)[N:17]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[NH2:35][CH:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:47])[S:43]([CH3:46])(=[O:45])=[O:44])[CH2:38][CH2:37]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:47][N:42]([CH:39]1[CH2:40][CH2:41][CH:36]([NH:35][C:18]2[N:17]=[C:16]([N:11]3[C:12]4[C:8](=[C:7]([CH2:6][O:5][CH2:4][CH2:3][S:2][CH3:1])[CH:15]=[CH:14][CH:13]=4)[CH:9]=[CH:10]3)[CH:21]=[CH:20][N:19]=2)[CH2:37][CH2:38]1)[S:43]([CH3:46])(=[O:44])=[O:45]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 21882552HCID 21882552, compoundHCID 69311986HCID 69311986, compound

Product 1

HCID 69309550HCID 69309550, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(2-Methylsulfanyl-ethoxymethyl)-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H indole (196 mg, 0.36 mmol) was dissolved in DCM, cooled on an ice bath, and MCPBA (635 mg, 2.83 mmol) was added and the mixture was stirred at RT overnight. The mixture was then diluted with DCM, washed with 5% NaHCO3, dried over sodium sulfate, filtered, concentrated in vacuo, and the residue dissolved in NMP and added to a suspension of N-(4-amino-cyclohexyl)-N-methyl-methanesulfonamide (409 mg, 1.98 mmol), 0.39 mL DIEA (2.27 mmol) and molecular sieves (previously stirred at RT for 1 h). The mixture was stirred at 120° C. for 1 h, cooled to RT, the mixture decanted into water, stirred for 30 min, filtered, and the precipitate purified by flash chromatography, eluting with DCM:MeOH 97:3. The product was then stirred in ether, filtered, and the solvent removed in vacuo overnight to yield N-methyl-N-(4-{4-[4-(2-methylsulfanyl-ethoxymethyl)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanesulfonamide (47 mg).

Workup

  1. temperaturecooled on an ice bath
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionthe residue dissolved in NMP
  7. stirringpreviously stirred at RT for 1 h)
  8. stirringThe mixture was stirred at 120° C. for 1 h
  9. temperaturecooled to RT
  10. customthe mixture decanted into water
  11. stirringstirred for 30 min
  12. filtrationfiltered
  13. customthe precipitate purified by flash chromatography
  14. washeluting with DCM:MeOH 97:3
  15. stirringThe product was then stirred in ether
  16. filtrationfiltered
  17. customthe solvent removed in vacuo overnight

Sources & evidence

ORD record
ord-643c4a50918842869ae3c655a5be4808
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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