Hydrochloric Acid → HCID 69308932, compound

HRID 2250588Notes

Reaction equation

HRID 2250588 reaction equation
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[Cl:29][C:30]1[N:34]2[N:35]=[C:36]([CH:48]([CH3:50])[CH3:49])[C:37](C=O)=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:33]2=[CH:32][CH:31]=1.Cl.[CH3:52]S(C)=O>>[Cl:29][C:30]1[N:34]2[N:35]=[C:36]([CH:48]([CH3:49])[CH3:50])[C:37](/[CH:52]=[CH:9]/[CH2:8][CH2:7][C:4]([OH:6])=[O:5])=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:33]2=[CH:32][CH:31]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromideHCID 86597470HCID 86597470, compound

Product 1

HCID 69308932HCID 69308932, compound

Conditions

Temperature
60 °C

Procedure

To dimethylsulfoxide (0.5 mL) was added 60% sodium hydride in oil (27 mg) and was heated at 60° C. for 40 minutes. To this mixture was added (3-carboxypropyl)(triphenyl)phosphonium bromide (124 mg) at ambient temperature and was stirred for 40 minutes. 7-Chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazine-3-carbaldehyde (40 mg) was added therein at ambient temperature. After 4 hours, the reaction mixture was acidified with 1N hydrogen chloride and was partitioned between ethyl acetate and water. The organic layer was washed with water three times and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by p-TLC (hexane-ethyl acetate=1-1) to give (4E)-5-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]-4-pentenoic acid as an yellow oil (21 mg, E:Z=16:1, 56.3%).

Workup

  1. customat ambient temperature
  2. waitAfter 4 hours
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water three times and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by p-TLC (hexane-ethyl acetate=1-1)

Sources & evidence

ORD record
ord-a3712f695294429f9f1d47f2c5e34616
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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