Water → HCID 9950403, compound

HRID 1005961Notes

Reaction equation

HRID 1005961 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[NH:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1)(C1C=CC(C)=CC=1)(=O)=O.[SH:27][C:28]1[NH:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1.C(N(CC)CC)C.O>C(#N)C>[N:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[NH:32][C:28]=1[S:27][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 22675452HCID 22675452, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 9950403HCID 9950403, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

188 mg of the compound obtained in Example 15a and 75 mg of 2-mercaptobenzimidazole were refluxed for 4 hours in 10 ml of acetonitrile containing 0.1 g of triethylamine. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 100m g of the title compound (yield: 57%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-91fa9e741d814dfbbd08ff3abefe0d24
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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