HCID 22054593, compound → HCID 22054594, compound

HRID 1006155Notes

Reaction equation

HRID 1006155 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:22])[CH:3]=1>N1CCCCC1>[CH3:22][C:4]1[CH:3]=[C:2]([N:5]2[CH2:6][CH2:11][CH2:2][CH2:3][CH2:4]2)[C:11]2[C:6](=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]=1

Participants

3

Reactant 1

HCID 22054593HCID 22054593, compound

Product 1

HCID 22054594HCID 22054594, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A solution of 4-(4-chloro-2-methyl-quinolin-7-ylmethoxy)-benzonitrile (example 54a, 100 mg, 0.32 mmol) in piperidine (1 mL) was heated at 100° C. for 21 h. After cooling the reaciton mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane, the organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 19:1) yielded the title compound (40 mg, 32%). Light yellow gum, ISP-MS: m/e=358.4 ([M+H]+).

Workup

  1. temperatureAfter cooling the reaciton mixture
  2. customwas partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-5b8a3835f70a4d74815d1aa19f5b12bb
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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