Ammonia → HCID 136346660, compound

HRID 2097380Notes

Reaction equation

HRID 2097380 reaction equation
C(OC[N:10]1[C:14]2[CH:15]=[N:16][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:18](=[O:19])[C:13]=2[C:12]([CH:28]([CH3:30])[CH3:29])=[C:11]1[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH:38]([F:40])[F:39])=[C:33]([O:41][CH:42]2[CH2:44][CH2:43]2)[CH:32]=1)C1C=CC=CC=1.N.[H][H]>[Pd].C(O)C>[CH:42]1([O:41][C:33]2[CH:32]=[C:31]([C:11]3[NH:10][C:14]4[CH:15]=[N:16][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])[C:18](=[O:19])[C:13]=4[C:12]=3[CH:28]([CH3:30])[CH3:29])[CH:36]=[CH:35][C:34]=2[O:37][CH:38]([F:40])[F:39])[CH2:44][CH2:43]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 66602501HCID 66602501, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136346660HCID 136346660, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 313 mg (0.500 mmol) of 1-benzyloxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-isopropyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 7-(a) were added 15 ml of ethanol, 1.6 ml of 28% aqueous ammonia and 39 mg of 5% palladium-active carbon, and the mixture was stirred under 1 atm hydrogen atmosphere at 30° C. for 7 days. After completion of the reaction, the reaction suspension was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; toluene:ethyl acetate=9:1→4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 152 mg of the title compound as a white foam. (Yield: 60%)

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction suspension was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionthe fractions containing the desired compound
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-f19bbc1b0abb4e139d0d2f99db556d2f
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

Loading…