Dichloromethane → HCID 66788407, compound

HRID 2261020Notes

Reaction equation

HRID 2261020 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][NH:10][C:9]2=[O:19])=[CH:4][CH:3]=1.[CH:20]1([CH2:25]O)[CH2:24][CH2:23][CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(Cl)[Cl:59]>>[CH:20]1([CH2:25][N:10]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]2=[O:19])[CH2:24][CH2:23][CH2:22][CH2:21]1.[ClH:59]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 77195CyclopentanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9964966HCID 9964966, compound2×

Product 1

HCID 66788407HCID 66788407, compound

Procedure

128 mg of 1-(4-Fluorophenyl)-5-(pyridin-4-yl)-4-imidazolin-2-one (the compound of Example 1), 61 μl of cyclopentylmethanol, 197 mg of triphenylphosphine and 295 μl of diethyl azodicarboxylate were dissolved in 2.5 ml of methylene chloride, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:ethyl acetate=19:1). The obtained compound was treated with hydrochloric acid, to give 75 mg of the title compound as powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=19:1)
  3. additionThe obtained compound was treated with hydrochloric acid

Sources & evidence

ORD record
ord-cf602f4e3ba74e108d6f3476d9fd8a37
Source dataset
uspto-grants-2010_12
Patent number
US07846933B2

Reaction notes

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