Diisopropylethylamine → HCID 53245737, compound

HRID 1025543Notes

Reaction equation

HRID 1025543 reaction equation
[OH:1][C:2]1[C:3]([C:12](Cl)=[O:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH2:15]1[CH:24]2[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:18][CH2:17][NH:16]1.CCN(C(C)C)C(C)C>C1COCC1>[OH:1][C:2]1[C:3]([C:12]([N:16]2[CH2:17][CH2:18][CH:19]3[CH:24]([CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:15]2)=[O:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 97812DecahydroisoquinolineHCID 15015183HCID 15015183, compound

Product 1

HCID 53245737HCID 53245737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 8-hydroxyquinoline-7-carbonyl chloride of Preparation 2 (70 mg, 0.35 mmol) and decahydroisoquinoline (62.6 mg, 0.45 mmol) in THF (8 mL) and DIPEA (259 mg, 2.0 mmol) was stirred and heated at 50° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between DCM and H2O. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, DCM:MeOH 98:2) and then by preparative HPLC. Product-containing fractions were combined, made basic with a saturated aqueous solution of sodium hydrogen carbonate and CH3CN was removed under reduced pressure. The aqueous phase was extracted with DCM and the separated organics dried over Na2SO4, filtered and concentrated to dryness, affording the title compound (49 mg, 0.16 mmol) as a off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between DCM and H2O
  3. dry with materialThe separated organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, DCM:MeOH 98:2)
  7. customwas removed under reduced pressure
  8. extractionThe aqueous phase was extracted with DCM
  9. dry with materialthe separated organics dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-69d750c087d14bb0b2df8de77f4f63a4
Source dataset
uspto-grants-2014_05
Patent number
US08729098B2

Reaction notes

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