Dichloromethane → HCID 178483521, compound

HRID 1798907Notes

Reaction equation

HRID 1798907 reaction equation
[CH2:1]([NH:8][C:9]([CH:11]1[CH2:21][N:20]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]2[C:29]3[C:12]1=[N:13][NH:14][C:15]=3[N:16]=[C:17](SC)[N:18]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=O)C=1.ClCCl.[CH3:46][N:47]([CH3:52])[CH2:48][CH2:49][CH2:50][NH2:51]>CS(C)=O>[CH2:1]([NH:8][C:9]([CH:11]1[C:12]2[C:29]3[C:15]([NH:14][N:13]=2)=[N:16][C:17]([NH:51][CH2:50][CH2:49][CH2:48][N:47]([CH3:52])[CH3:46])=[N:18][C:19]=3[N:20]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 70297m-Chloroperbenzoic acidHCID 178503324HCID 178503324, compound

Product 1

HCID 178483521HCID 178483521, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N,5-dibenzyl-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene-3carboxamide (0.065 g, 0.15 mmol), 3-chloroperbenzoic acid (0.057 g, 0.33 mmol), and dichloromethane (3 mL) were placed in a screw top 2-dram vial and shaken at room temperature for 4 hours. The reactions were quenched by addition of sat NaHCO3 (2 mL). The layers were separated and the organic layers was washed with water (2×3 mL). The organic layer was concentrated under reduced pressure in Genevac centrifugal evaporation system. To the vials containing sulfone were placed N1,N1-dimethylpropane-1,3-diamine (0.45 mmol) and DMSO (1 mL). The vials were capped and shaken at 120° C. for 10 hours. The crude product was purified using reverse phase column chromatography using a Maccel AQ C18 column and a gradient of 1-95% ACN/water containing 0.05% trifluoroacetic acied, to yield the desired products in acceptable purities by LC/MS. LC-Mass: m/e 485 (M+1).

Workup

  1. customThe reactions were quenched by addition of sat NaHCO3 (2 mL)
  2. customThe layers were separated
  3. washthe organic layers was washed with water (2×3 mL)
  4. concentrationThe organic layer was concentrated under reduced pressure in Genevac centrifugal evaporation system
  5. additionTo the vials containing sulfone
  6. customThe vials were capped
  7. stirringshaken at 120° C. for 10 hours
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-a4d0eb6ecd134a3688a374b3ba963333
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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