3-Cyclobutoxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → 2-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-ethylpropoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097447Notes

Reaction equation

HRID 2097447 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[NH:32][C:18]4[CH:19]=[N:20][N:21](COCC[Si](C)(C)C)[C:22](=[O:23])[C:17]=4[C:16]=3[CH2:33][O:34][CH:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:14])[F:13])[CH2:3][CH2:2]1.C1(OCC2C3C(=O)N(COCC[Si](C)(C)C)N=CC=3NC=2C2C=CC(OC(F)F)=C(OC3CC3)C=2)CCC1>>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[NH:32][C:18]4[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=4[C:16]=3[CH2:33][O:34][CH:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:13])[F:14])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 1363466633-Cyclobutoxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 1363466802-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-ethylpropoxymethyl)-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 1363466812-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-ethylpropoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 35%

Procedure

Reaction and post treatment were carried out in the same manner as in Example 13-(c) except for using 0.26 g (0.46 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-ethylpropoxymethyl)-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 65-(b) in place of 3-cyclobutoxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one, whereby 69 mg of the title compound was obtained as a white solid. (Yield: 35%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-b44577b3f62b49009c0648aead7c2926
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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