Water → HCID 44193375, compound

HRID 1855458Notes

Reaction equation

HRID 1855458 reaction equation
[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]([NH2:26])=[NH:25])[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=O)[C:35]#[C:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:30][CH:29]=1.C[O-].[Na+].O>C(#N)C>[CH2:37]([C:36]1[CH:35]=[C:34]([C:31]2[CH:30]=[CH:29][C:28]([Cl:27])=[CH:33][CH:32]=2)[N:26]=[C:24]([NH:23][C:13]2[CH:14]=[CH:15][C:16]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:11]([O:10][CH3:9])[CH:12]=2)[N:25]=1)[CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 13552876HCID 13552876, compoundHCID 178493228HCID 178493228, compound

Product 1

HCID 44193375HCID 44193375, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of N-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (153 mg, 0.41 mmol), 1-(4-chloro-phenyl)-hept-2-yn-1-one (100 mg, 0.45 mmol, CAS 105363-17-5) and sodium methanolat (120 mg, 1.24 mmol) in acetonitrile (2.0 mL) was heated two times to 120° C. for 30 minutes in a microwave oven. Water was added and the reaction was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography on silica gel using dichloromethane/methanol (9:1 v/v) as eluent to yield the title compound as a yellow solid (30 mg, 16%). MS ISP (m/e): 448.3/450.1 (100/37) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.04 (d, 2H), 7.98 (s, 1H), 7.64 (s, 1H), 7.46 (d, 2H), 7.29 (s, 1H), 7.18 (d, 1H), 7.04 (d, 1H), 6.89 (s, 1H), 3.89 (s, 3H), 2.74 (t, 2H), 2.31 (, 3H), 1.79 (m, 2H), 1.43 (m, 2H), 0.98 (t, 3H).

Workup

  1. extractionthe reaction was extracted twice with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3d43ecc2047b42b5917bf584948495df
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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