2-Methyl-2-butene → HCID 68725206, compound

HRID 1875264Notes

Reaction equation

HRID 1875264 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([CH:25]=[O:26])[CH:22]=[C:21]([C:27]#[N:28])[CH:20]=2)[C:12]=1[F:29])=[O:8].CC(=CC)C.Cl([O-])=[O:44].[Na+].[H-].P(O)(O)(O)=O.[Na+]>O>[Cl:17][C:14]1[C:13]([O:18][C:19]2[CH:24]=[C:23]([CH:22]=[C:21]([C:27]#[N:28])[CH:20]=2)[C:25]([OH:44])=[O:26])=[C:12]([F:29])[C:11]([CH2:10][NH:9][C:7]([C:6]2[N:5]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:4]=[N:3][C:2]=2[Cl:1])=[O:8])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 105532-Methyl-2-buteneHCID 3084021HCID 3084021, compoundHCID 23668197Sodium ChloriteHCID 86644952HCID 86644952, compound

Product 1

HCID 68725206HCID 68725206, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-chloro-N-({4-chloro-3-[(3-cyano-5-formylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (200 mg, 0.355 mmol) in 2-methyl-2-butene (4.44 ml, 4.44 mmol) was added a solution of sodium chlorite (401 mg, 3.55 mmol) and sodium dihydrogenphosphate monohydride (302 mg, 2.130 mmol) in water (2 mL). The mixture was stirred for 4 hours and the solvent was removed under vacuum. The residue was diluted with EtOAc and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by reverse phase HPLC (MeCN/water 0.1% formic acid) to give 130 mg (63%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.78 (t, 1H), 7.88-8.14 (m, 2H), 7.81 (s, 1H), 7.31-7.61 (m, 3H), 5.49 (s, 2H), 4.35-4.59 (m, 2 H), 3.31 (s, 2H), 0.57-0.85 (m, 2H), −0.09 (s, 9H). LC-MS (ES+) m/z 578.25, [M+H].

Workup

  1. customthe solvent was removed under vacuum
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by reverse phase HPLC (MeCN/water 0.1% formic acid)

Sources & evidence

ORD record
ord-ffb5c15e88ab40b6857b5f4bfc7c6d13
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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