Water → HCID 58303086, compound

HRID 587395Notes

Reaction equation

HRID 587395 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[NH:10]1[CH2:20][CH2:19][CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11]1.O>C1(C)C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:17]([O:16][C:14]([CH:13]1[CH2:19][CH2:20][N:10]([C:2]2[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=2)[CH2:11][CH2:12]1)=[O:15])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 70770Ethyl 4-piperidinecarboxylateHCID 744033-Chloro-6-methoxypyridazine

Product 1

HCID 58303086HCID 58303086, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.33 g (30 mmol) 3-chloro-6-methoxypyridazine, 5.66 g (36 mmol) ethyl isonipecotate, 3.46 g (36 mmol) sodium tert.-butylate, 0.56 g (0.9 mmol) BINAP amd 0.55 g (0.5 mmol) Pd2 dba3 in 60 mL toluene was heated to 100° C. for 90 min. After cooling to room temperature water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried with Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient formed from heptane and ethyl acetate. The product containing fractions were evaporated to yield 3.2 g (34%) of the title compound as orange solid. MS m/e: 266.3 [M+H]+.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica eluting with a gradient
  8. customformed from heptane and ethyl acetate
  9. additionThe product containing fractions
  10. customwere evaporated

Sources & evidence

ORD record
ord-5831cfda0b32493eaa508c3a7380d319
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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