Water → HCID 23654206, compound

HRID 1785515Notes

Reaction equation

HRID 1785515 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([OH:21])[C:18]([OH:20])=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5])C.[CH3:28][O:29][CH2:30][CH2:31]Br.[C:33](=[O:36])([O-])[O-].[K+].[K+].O.CN1CC[CH2:43][C:42]1=O>>[CH3:28][O:29][CH2:30][CH2:31][O:20][C:18]1[C:17]([O:21][CH2:42][CH2:43][O:36][CH3:33])=[CH:16][C:15]2[N:11]([C:9]3[S:10][C:6]([C:4]([OH:3])=[O:5])=[C:7]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:8]=3)[CH:12]=[N:13][C:14]=2[CH:19]=1

Participants

6

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 809722-Bromoethyl methyl etherHCID 23653658HCID 23653658, compound

Product 1

HCID 23654206HCID 23654206, compoundYield 17%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(5,6-dihydroxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (118.8 mg, 0.31 mmol, intermediate for Example 39), bromoethyl methyl ether (0.1 ml) and potassium carbonate (200 mg) in N-methylpyrrolidone (2 ml) was stirred at RT overnight and 80° C. for 4 hr. Water was added, and the mixture was extracted with ethyl acetate. After removal of solvent, the residue was diluted with methanol (3 ml) and sodium hydroxide solution (1N, 1.5 ml) was added. The mixture was stirred at RT for 105 min. Methanol was removed, the aqueous was neutralized to pH 3. The precipitate was collected and purified by preparative HPLC to give the desired product (24.6 mg, yield 17%). 1H-NMR (DMSO-D6) 8.71 (s, 1H); 8.20-8.27 (m, 2H); 7.83 (s, 1H); 7.24-7.41 (m, 3H); 4.17-4.22 (m, 4H); 3.66-3.75 (m, 4H); 3.33 (s, 6H). MS M/z 470 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customAfter removal of solvent
  3. additionthe residue was diluted with methanol (3 ml) and sodium hydroxide solution (1N, 1.5 ml)
  4. additionwas added
  5. stirringThe mixture was stirred at RT for 105 min
  6. customMethanol was removed
  7. customThe precipitate was collected
  8. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-e85216952b934b1c8df0c3f4ada64753
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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