Imidazole → HCID 23144369, compound

HRID 337402Notes

Reaction equation

HRID 337402 reaction equation
Br[CH2:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[O:8])=[CH:5][CH:4]=1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.O>CN1C(=O)CCC1>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:13]1[N:14]=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([CH2:2][N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[CH:27][CH:26]=2)[S:11][C:12]=1[C:20]1[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 23144096HCID 23144096, compound

Product 1

HCID 23144369HCID 23144369, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
65 °C

Procedure

Compound 18 (880 mg, 2.00 mmol) was suspended in NMP (10 mL), and imidazole (408 mg, 6.00 mmol) was added thereto, followed by stirring at 65° C. for 2 hours. The reaction mixture was allowed to cool down to room temperature and then poured into water, and the deposited precipitate was collected by filtration. The resulting precipitate was purified through silica gel column chromatography (chloroform:methanol=17:3) to afford the entitled Compound 19 (538 mg, 63%).

Workup

  1. temperatureto cool down to room temperature
  2. filtrationthe deposited precipitate was collected by filtration
  3. customThe resulting precipitate was purified through silica gel column chromatography (chloroform:methanol=17:3)

Sources & evidence

ORD record
ord-d010328129584fd1a8994391a3f3a846
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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