Tetrahydrofuran → HCID 66602776, compound

HRID 2097382Notes

Reaction equation

HRID 2097382 reaction equation
O1CCCC1.[CH:6]1([O:9][C:10]2[CH:11]=[C:12]([C:20]3[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:23]4[CH:24]=[N:25][NH:26][C:27](=[O:28])[C:22]=4[C:21]=3[CH:38]=[O:39])[CH:13]=[CH:14][C:15]=2[O:16][CH:17]([F:19])[F:18])[CH2:8][CH2:7]1.[BH4-].[Na+]>O>[CH:6]1([O:9][C:10]2[CH:11]=[C:12]([C:20]3[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:37])[CH3:36])[C:23]4[CH:24]=[N:25][NH:26][C:27](=[O:28])[C:22]=4[C:21]=3[CH2:38][OH:39])[CH:13]=[CH:14][C:15]=2[O:16][CH:17]([F:19])[F:18])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 866270302-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-formyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 66602776HCID 66602776, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3 ml of tetrahydrofuran solution containing 221 mg (0.450 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-formyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 10-(a) was added 58 mg (1.53 mmol) of sodium borohydride under ice-cooling, and the reaction mixture was raised to room temperature. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed successively with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 155 mg of the title compound as a pale yellowish foam. (Yield: 70%)

Workup

  1. temperaturecooling
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer after separation
  5. washwas washed successively with water
  6. dry with materialwith a 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-73da2e97272b44b7821f5d5495092e2a
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

Loading…