3-Chloro-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → 2-(8-Difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-ethyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one HCl

HRID 2097436Notes

Reaction equation

HRID 2097436 reaction equation
[F:1][CH:2]([F:36])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:16]2[NH:33][C:19]3[CH:20]=[N:21][N:22](COCC[Si](C)(C)C)[C:23](=[O:24])[C:18]=3[C:17]=2[CH2:34][CH3:35])=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH:10]=[CH:9]2.[Cl:37]C1C2C(=O)NN=CC=2N(COCC[Si](C)(C)C)C=1C1C=CC(OC(F)F)=C(OC2CC2)C=1>>[ClH:37].[F:36][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:16]2[NH:33][C:19]3[CH:20]=[N:21][NH:22][C:23](=[O:24])[C:18]=3[C:17]=2[CH2:34][CH3:35])=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH:10]=[CH:9]2

Participants

3

Reactant 2

HCID 666026343-Chloro-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 1363373522-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-ethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1363466752-(8-Difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-ethyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one HClYield 93%

Procedure

Reaction was carried out in the same manner as in Example 6-(c) except for using 613 mg (1.18 mmol) of 2-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-ethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 54-(b) in place of 3-chloro-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one. After completion of the reaction, the solid obtained from the reaction suspension by filtration was washed with hexane and dried under reduced pressure to obtain 467 mg of the title compound as a white solid. (Yield: 93%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. customthe solid obtained from the reaction suspension by filtration
  4. washwas washed with hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c4f3528ae270487ba5ee0c0aa7a4456e
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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