Potassium Carbonate → HCID 86644953, compound

HRID 1875187Notes

Reaction equation

HRID 1875187 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)[CH:22]=[C:21]([C:27]#[N:28])[CH:20]=2)[C:12]=1[F:29])=[O:8].[C:38](=O)([O-])[O-].[K+].[K+].CC(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-]>CO.CCOC(C)=O>[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]([C:25]#[CH:38])[CH:22]=[C:21]([C:27]#[N:28])[CH:20]=2)[C:12]=1[F:29])=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonateHCID 86644952HCID 86644952, compound

Product 1

HCID 86644953HCID 86644953, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

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 (90 mg, 0.160 mmol) and potassium carbonate (66.2 mg, 0.479 mmol) in Methanol (5 ml) was added dimethyl-1-diazo-2-oxopropylphosphonate (46.0 mg, 0.240 mmol) and the reaction mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-({4-chloro-3-[(3-cyano-5-ethynylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (48 mg, 0.086 mmol, 54% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.87 (s, 1H), 7.54 (s, 1H), 7.31-7.45 (m, 2H), 7.25 (s, 1H), 7.20 (s, 1H), 5.57 (s, 3H), 4.59 (s, 2H), 3.75 (s, 1H), 3.47 (t, 2H), 0.80 (t, 2H), −0.07 (s, 9H).

Workup

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-88bc5d5c1db6421c82f6c0505cb736ce
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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