Dichloromethane → HCID 67515583, compound

HRID 1619438Notes

Reaction equation

HRID 1619438 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20][CH2:19]3)=[CH:14][CH:13]=2)[N:5]=[CH:4][N:3]=1.Cl.[CH:27]([C:30]1[N:34]=[C:33]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[O:32][N:31]=1)([CH3:29])[CH3:28].ClCCl>>[CH3:24][C:21]1([CH3:25])[O:22][CH2:23][CH:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][C:6]3[N:5]=[CH:4][N:3]=[C:2]([N:38]4[CH2:37][CH2:36][CH:35]([C:33]5[O:32][N:31]=[C:30]([CH:27]([CH3:29])[CH3:28])[N:34]=5)[CH2:40][CH2:39]4)[C:7]=3[N+:8]([O-:10])=[O:9])=[CH:13][CH:14]=2)[CH2:19][O:20]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 534008274-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidine hydrochlorideHCID 86665162HCID 86665162, compound

Product 1

HCID 67515583HCID 67515583, compoundYield 66%

Conditions

Temperature
27 °C

Procedure

To an ice-cold solution of 4-chloro-6-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidine (500 mg, 0.0013 moles) and 3-isopropyl-5-(piperidin-4-yl)-1,2,4-oxadiazole hydrochloride (293 mg, 0.0015 mole) in dichloromethane (10 ml) diisopropyl ethyl amine (0.24 ml, 0.0016 mole) was added and the reaction mixture was stirred for 4 hours at 27° C. The reaction mixture was poured into ice cold water and extracted with dichloromethane. The organic extract was successively washed with water & brine, dried over calcium chloride and evaporated under reduced pressure. The crude product so obtained was purified by column chromatography using 20% ethyl acetate in hexane as eluent to yield 450 mg product as pale yellow solid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas successively washed with water & brine
  5. dry with materialdried over calcium chloride
  6. customevaporated under reduced pressure
  7. customThe crude product so obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-25255abac72e45898cbf07f7411bd635
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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