Ammonium Chloride → 1-Benzyloxymethyl-3-isopropyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097502Notes

Reaction equation

HRID 2097502 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[N:16][NH:17][C:18](=[O:19])[C:13]=2[C:12]([CH:20]([CH3:22])[CH3:21])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Si:24]([CH3:40])([CH3:39])[CH2:25][CH2:26][O:27][CH2:28]N1C2C=NNC(=O)C=2C=C1.[Cl-].[NH4+]>>[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[N:16][N:17]([CH2:28][O:27][CH2:26][CH2:25][Si:24]([CH3:40])([CH3:39])[CH3:23])[C:18](=[O:19])[C:13]=2[C:12]([CH:20]([CH3:22])[CH3:21])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 666025541-Benzyloxymethyl-3-isopropyl-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-oneHCID 666030201-(2-Trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666027061-Benzyloxymethyl-3-isopropyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 62%

Procedure

Reaction was carried out in the same manner as in Reference example 18-(a) except for using 0.98 g (3.3 mmol) of 1-benzyloxymethyl-3-isopropyl-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one obtained in Reference example 21-(e) in place of 1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one. After completion of the reaction, the reaction mixture was poured into ice-water, neutralized with a saturated aqueous solution of ammonium chloride and extracted with toluene. The organic layer after separation was washed successively with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=3:2 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.87 g of the title compound as a slightly yellowish oil. (Yield: 62%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. customThe organic layer after separation
  5. washwas washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a88228cbfeb4a67b951a34484643c09
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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