Methyl iodide → HCID 58659432, compound

HRID 1993563Notes

Reaction equation

HRID 1993563 reaction equation
IC.[NH:3]1[C:7]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)=[O:23])=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[N:6][N:5]=[N:4]1.[C:35](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:35][N:6]1[C:7]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[CH:26]=4)=[O:23])=[CH:19][CH:20]=3)[CH:11]=[CH:10][N:9]=2)=[N:3][N:4]=[N:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522230HCID 178522230, compound

Product 1

HCID 58659432HCID 58659432, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Iodomethane (0.21 mL, 3.40 mmol, 1.5 equiv) is added to a cold (0° C.) mixture of 1-{4-[2-(1H-tetrazol-5yl)-pyridin-4-yloxy]-phenyl}-3-(3-trifluoromethyl-phenyl)-urea (Example 122) (1.0 g, 2.27 mmol) and potassium carbonate (0.94 g, 6.80 mmol, 3.0 equiv) in DMF abs. (5.8 mL), under an argon atmosphere. The reaction mixture is stirred at 0° C. for 2 h, allowed to warm to rt and stirred for additional 20 h. The resulting brown suspension is filtered and concentrated in vacuo. MeOH (10 mL) and DMF (0.5 mL) are added to the residue and the resulting suspension is filtered. The white solid is washed with MeOH and dried in vacuo to afford the title compound as a white solid. The filtrate is concentrated in vacuo and the residue is purified by MPLC (CH3CN/H2O/TFA) to afford additional title compound as a beige solid: ES-MS: 455.9 [M+H]+; single peak at tR=9.15 min (System 2).

Workup

  1. temperatureto warm to rt
  2. stirringstirred for additional 20 h
  3. filtrationThe resulting brown suspension is filtered
  4. concentrationconcentrated in vacuo
  5. additionMeOH (10 mL) and DMF (0.5 mL) are added to the residue
  6. filtrationthe resulting suspension is filtered
  7. washThe white solid is washed with MeOH
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6d0f3edb794e482987e92c883c41ab68
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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