Dichloromethane → HCID 178456090, compound

HRID 80581Notes

Reaction equation

HRID 80581 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([CH:33]=1)[CH2:7][C@H:8]1[C:14](=[O:15])[N:13]([C:16]([NH:18][C@H:19]([CH2:23][CH3:24])[C:20]([OH:22])=O)=[O:17])[CH2:12][C:11](=[N:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:10][CH2:9]1.C(Cl)Cl.C(C1NC=CN=1)(C1[NH:42]C=CN=1)=O.[NH4+].[OH-]>C(Cl)(Cl)Cl>[C:20]([C@H:19]([NH:18][C:16]([N:13]1[C:14](=[O:15])[C@H:8]([CH2:7][C:6]2[CH:33]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:34][CH3:35])[CH2:9][NH:10][C:11](=[N:25][O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:12]1)=[O:17])[CH2:23][CH3:24])(=[O:22])[NH2:42]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 178456092HCID 178456092, compound

Product 1

HCID 178456090HCID 178456090, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the compound 54 (114 mg) in a methylene chloride (2 ml) solution, carbonyl diimidazole (45 mg) was added, and the mixture was stirred at room temperature for 45 minutes. The reaction solution was cooled to 0° C., then 28% ammonia aqueous solution (2 ml) was added, and the mixture was stirred at that temperature for 1 hour. The reaction solution was diluted with chloroform and the resultant mixture successively washed with water, 1M hydrochloric acid, and brine. The organic layer was dried over anhydrous sodium sulfate, then was concentrated. The residue was purified by flash column chromatography (silica gel, chloroform/ethyl acetate=7/3 to 1/2) to obtain the title compound (40 mg).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringthe mixture was stirred at that temperature for 1 hour
  3. washthe resultant mixture successively washed with water, 1M hydrochloric acid, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationwas concentrated
  6. customThe residue was purified by flash column chromatography (silica gel, chloroform/ethyl acetate=7/3 to 1/2)

Sources & evidence

ORD record
ord-6b14c3d51b5842f1b2f1a74fefece3e2
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

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