HCID 59324073, compound → HCID 59324070, compound

HRID 2063686Notes

Reaction equation

HRID 2063686 reaction equation
C(OC([C:6]1[N:7]=[C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]3)=[C:14]([O:24][CH3:25])[CH:13]=2)[S:9][CH:10]=1)=O)C.C[Mg]Br>C1COCC1>[CH3:25][O:24][C:14]1[CH:13]=[C:12]([NH:11][C:8]2[S:9][CH:10]=[C:6]([C:14]([OH:24])([CH3:15])[CH3:13])[N:7]=2)[CH:17]=[CH:16][C:15]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1

Participants

4

Reactant 2

HCID 59324073HCID 59324073, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59324070HCID 59324070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazole-4-carboxylic acid ethyl ester (20 mg, 0.056 mmol) in dry THF (2 ml) at 0° C. was added methylmagnesium bromide (3M solution in THF, 93 μl, 0.279 mmol) added and stirred at 0° C. for 2 h. The reaction mixture was cautiously quenched with saturated aqueous ammonium chloride solution. The aqueous phase was extracted three times with diethyl ether, dried over Na2SO4, filtered and the solvents were evaporated. The residue was purified by silica gel chromatography using dichloromethane/methanol as eluent. The title compound was obtained as a light brown oil (14.4 mg, 75%). MS ISP (m/e): 345.1 (100) [(M+H)+].

Workup

  1. additionadded
  2. customThe reaction mixture was cautiously quenched with saturated aqueous ammonium chloride solution
  3. extractionThe aqueous phase was extracted three times with diethyl ether
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were evaporated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5cd6cb020ec640cd9db71d5e49956340
Source dataset
uspto-grants-2012_10
Patent number
US08288403B2

Reaction notes

Loading…