Dimethylamine → HCID 66602821, compound

HRID 2097409Notes

Reaction equation

HRID 2097409 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]4[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=4[C:16]=3[CH:33]=O)[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:14])[F:13])[CH2:3][CH2:2]1.O1CCCC1.[CH3:40][NH:41][CH3:42].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]4[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=4[C:16]=3[CH2:33][N:41]([CH3:42])[CH3:40])[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:13])[F:14])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 866270302-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-formyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 66602821HCID 66602821, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 133 mg (0.270 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) and 112 mg of Molecular sieve (3A) was added 5 ml of tetrahydrofuran solution containing 2M dimethylamine at room temperature, and the mixture was stirred for 10 minutes. Then, 156 mg (0.740 mmol) of sodium triacetoxyborohydride was added to the mixture, and the mixture was stirred for further 17 hours. 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; ethyl acetate→chloroform:methanol=4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 74 mg of the title compound as a pale yellowish solid. (Yield: 53%)

Workup

  1. stirringthe mixture was stirred for further 17 hours
  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-64cf5481b28145399b52fb7c4f0f09f0
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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