Methyl iodide → HCID 46890031, compound

HRID 1453683Notes

Reaction equation

HRID 1453683 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19](=[O:27])(=[O:26])[NH:18]2)=[CH:9]1)(C)(C)C.[C:29]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:29][N:18]1[CH:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][C:6]([OH:5])=[O:28])[CH:9]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:19]1(=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67316103HCID 67316103, compound

Product 1

HCID 46890031HCID 46890031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The intermediate from example 1, step d (33 mg, 0.08 mmol) was dissolved in DMF (1 mL) and treated with K2CO3 (28 mg, 0.2=nmol) followed by methyl iodide. The reaction was heated to 70°-80° C. for 1 h. The reaction mixture was cooled and partitioned between EtOAc and water. The organic layer was washed several times with water then concentrated to dryness. The crude residue was then treated with TFA (2 mL) for 2 h. The reaction was concentrated and purified by preparative LCMS to give the title compound. 1H NMR (DMSO-d6) δ 8.22-8.20 (m, 1H), 7.88-7.85 (m, 2H), 7.81 (s, 1H), 7.54 (d, J=8.1 Hz, 1H), 7.40-7.35 (m, 1H), 7.28 (t, J=7.5 Hz, 1H), 7.17 (d, J=7.8 Hz, 1H), 7.05 (t, J=7.2 Hz, 1H), 5.94 (s, 1H), 4.80 (s, 2H), 2.88 (s, 3H); MS: ESI (negative): 355 (M−H).

Workup

  1. temperatureThe reaction was heated to 70°-80° C. for 1 h
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed several times with water
  5. concentrationthen concentrated to dryness
  6. additionThe crude residue was then treated with TFA (2 mL) for 2 h
  7. concentrationThe reaction was concentrated
  8. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-2d6176db6931496b90085995ad0291a3
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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