Chloromethyl Methyl Ether → HCID 66580218, compound

HRID 1521844Notes

Reaction equation

HRID 1521844 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])=[N:14][N:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1)(=[O:10])=[O:9].[H-].[Na+].[CH3:33][O:34][CH2:35]Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH2:33][O:34][CH3:35])[C:12]1[C:13]([C:23]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[O:24])=[N:14][N:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 66581050HCID 66581050, compound

Product 1

HCID 66580218HCID 66580218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-N-[3-(morpholin-4-ylcarbonyl)-1-phenyl-1H-pyrazol-4-yl]benzenesulfonamide (200 mg; 0.41 mmol; 1.00 eq.) in THF (30 mL) is added NaH (24 mg; 0.61 mmol; 1.50 eq.) in a portionwise manner and the resulting mixture is stirred at room temperature for 15 minutes whereupon Chloromethyl methyl ether (82 μl; 0.81 mmol; 2.00 eq.) is added dropwise. The reaction mixture is stirred at room temperature for 2 hours then quenched with sat. aq. NaHCO3. Extraction with ethyl acetate (2×), ishing with brine, drying over magnesium sulfate and concentration in vacuo gives 240 mg (quant) of the title compound as a colourless oil. 1H NMR (DMSO) δ 8.82 (s, 1H), 7.93-7.8 (m, 4H), 7.64-7.46 (m, 4H), 7.39 (t, J=7.4 Hz, 1H), 5.32 (s, 2H), 3.59-3.51 (m, 2H), 3.42 (s, 3H), 3.46-3.37 (m, 4H), 3.15-3.06 (m, 2H). MS (ESI+): 505.2.

Workup

  1. additionis added dropwise
  2. customthen quenched with sat. aq. NaHCO3
  3. extractionExtraction with ethyl acetate (2×)
  4. dry with materialdrying over magnesium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-9f025f9eeb4a49c9b6457939c6af26d4
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

Loading…