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-methyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one HCl

HRID 2097434Notes

Reaction equation

HRID 2097434 reaction equation
[F:1][CH:2]([F:35])[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[CH3:34])=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH:10]=[CH:9]2.[Cl:36]C1C2C(=O)NN=CC=2N(COCC[Si](C)(C)C)C=1C1C=CC(OC(F)F)=C(OC2CC2)C=1>>[ClH:36].[F:35][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[CH3:34])=[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 1363466732-(8-Difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-methyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1363466742-(8-Difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-methyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one HClYield 84.6%

Procedure

Reaction was carried out in the same manner as in Example 6-(c) except for using 163 mg (0.323 mmol) of 2-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-methyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one obtained in Example 53-(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 diisopropyl ether and dried under reduced pressure to obtain 112 mg of the title compound as a white solid. (Yield: 84.6%)

Workup

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

Sources & evidence

ORD record
ord-071dea2f66b44c74857e1379081675e2
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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