Methyl morpholine oxide → HCID 11247510, compound

HRID 2216317Notes

Reaction equation

HRID 2216317 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[C:16]([NH:22][C:23]3[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=3[CH3:31])=[N:17][C:18]([CH3:21])=[N:19][CH:20]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.C[N+]1([O-])CCOCC1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.C(Cl)Cl>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([S:12]([C:15]2[C:16]([NH:22][C:23]3[C:24]([CH3:31])=[CH:25][C:26]([CH3:30])=[CH:27][C:28]=3[CH3:29])=[N:17][C:18]([CH3:21])=[N:19][CH:20]=2)(=[O:13])=[O:14])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 11235910HCID 11235910, compound

Product 1

HCID 11247510HCID 11247510, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of {5-[4-(4,5-dihydro-1H-imidazol-2-yl)-benzenesulfonyl]-2-methyl-pyrimidin-4-yl}-(2,4,6-trimethyl-phenyl)-amine (14 mg, 0.032 mmol), prepared by the method described in Example 29, NMO (5.6 mg, 0.048 mmol), TPAP (2.2 mg, 0.006 mmol), 4 Å molecular sieves (100 mg) and CH2Cl2 (2 mL) was stirred under N2 at room temperature for 10 min, and then filtered through a pad of silica gel. The filtrate was concentrated in vacuo, and the residue was purified by chromatography on silica gel (EtOAc) to provide the target compound (5 mg, 36%) as a white solid: mp 282–284° C.; 1H NMR (500 MHz, CDCl3) δ 9.54 (br s, 1H), 8.78 (s, 1H), 8.27 (br s, 1H), 8.02 (d, J=8.5 Hz, 2H), 7.99 (d, J=8.5 Hz, 2H), 7.28 (s, 1H), 7.18 (s, 1H), 6.91 (s, 2H), 2.40 (s, 3H), 2.30 (s, 3H), 2.02 (s, 6H); ESI MS m/z 434 [(M+H)+, calcd for C23H24N5O2S, 434.2].

Workup

  1. customprepared by the method
  2. filtrationfiltered through a pad of silica gel
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-3e90a8b1d4be40e9873a68d2789d7dfd
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

Loading…