Tetrahydrofuran → 3-Chloro-2-(3-cyclopropoxy-4-methoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097424Notes

Reaction equation

HRID 2097424 reaction equation
[Cl:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][N:7]=[CH:6][C:5]=2[N:4](COCC[Si](C)(C)C)[C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH:29]2[CH2:31][CH2:30]2)[CH:21]=1.C1(OC2C=C(C3N(COCC[Si](C)(C)C)C4C=NNC(=O)C=4C=3)C=CC=2OC(F)F)CC1.O1CCCC1>O.CO>[Cl:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][N:7]=[CH:6][C:5]=2[NH:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH:29]2[CH2:30][CH2:31]2)[CH:21]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 666024612-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028673-Chloro-2-(3-cyclopropoxy-4-methoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1356204673-Chloro-2-(3-cyclopropoxy-4-methoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Reaction was carried out in the same manner as in Example 1-(b) except for using 313 mg (0.677 mmol) of 3-chloro-2-(3-cyclopropoxy-4-methoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 42-(a) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one. After completion of the reaction, water was added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained crude solid was dissolved by adding small amounts of tetrahydrofuran and methanol, followed by addition of water, and the solid precipitated by ultrasonic wave treatment was collected by filtration. The obtained solid was washed with water and dried under reduced pressure to obtain 136 mg of the title compound as a white solid. (Yield: 61%)

Workup

  1. customReaction
  2. additionwas added to the reaction mixture
  3. filtrationthe precipitated solid was collected by filtration
  4. customThe obtained crude solid
  5. dissolutionwas dissolved
  6. customthe solid precipitated by ultrasonic wave treatment
  7. filtrationwas collected by filtration
  8. washThe obtained solid was washed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-4d4eb3159c0e4a1e9ab0f5b96eda431b
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

Loading…