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Hydrochloric Acid → 1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-n-(4-methyl-6-(5-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide

HRID 869942
Notes
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Reaction equation

HRID 869942 reaction equation
[F:1][C:2]1([F:33])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[CH:24]=[N:25][C:26]([O:30]C)=[C:27]([CH3:29])[CH:28]=5)[CH:20]=[C:19]([CH3:32])[CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.Cl>O1CCOCC1>[F:33][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[C:19]([CH3:32])[CH:20]=[C:21]([C:23]5[CH:28]=[C:27]([CH3:29])[C:26](=[O:30])[NH:25][CH:24]=5)[N:22]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 710530861-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)-N-(6'-methoxy-4,5'-dimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

Product 1

HCID 687396721-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-n-(4-methyl-6-(5-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamideYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6′-methoxy-4,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (0.075 g, 0.165 mmol) in 1,4-dioxane (2 mL) was added aqueous 4 M HCl (447 μL, 1.79 mmol) drop-wise. The reaction was stirred at 90° C. for 1.5 hours. The reaction was allowed to cool down to room temperature and then quenched with Et3N. The solvent was evaporated under reduced pressure. The crude compound was dissolved in ethyl acetate and washed with water (2×) and brine (1×). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(4-methyl-6-(5-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide as a white solid (33 mg, 46%); ESI-MS m/z calc. 439.41. found 440.5 (M+1)+. Retention time 1.72 minutes.

Workup

  1. temperatureto cool down to room temperature
  2. customquenched with Et3N
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionThe crude compound was dissolved in ethyl acetate
  5. washwashed with water (2×) and brine (1×)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b7f7601ccec34456b8d950a8636fe79b
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969386B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes