Triethylamine → HCID 69081423, compound

HRID 244821Notes

Reaction equation

HRID 244821 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])[CH:2]=[CH2:3].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:40]1[CH:49]=[CH:48][C:47]2[N:46]=[C:45]([NH2:50])[C:44]3[N:51]=[CH:52][N:53]([CH2:54][CH:55]([CH3:57])[CH3:56])[C:43]=3[C:42]=2[CH:41]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[NH2:50][C:45]1[C:44]2[N:51]=[CH:52][N:53]([CH2:54][CH:55]([CH3:57])[CH3:56])[C:43]=2[C:42]2[CH:41]=[C:40](/[CH:3]=[CH:2]/[CH2:1][N:4]3[CH2:8][CH2:7][CH2:6][C:5]3=[O:9])[CH:49]=[CH:48][C:47]=2[N:46]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 758971-(Allyl)pyrrolidin-2-oneHCID 80271Tri-o-tolylphosphineHCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 69081423HCID 69081423, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A thick walled glass tube, equipped with stir bar, was charged with palladium (II) acetate (67 mg, 0.3 mmol), acetonitrile (15 mL), N-allyl-2-pyrrolidone (650 mg, 5.17 mmol), triethylamine (2.1 ml, 15.65 mmol), tri-o-tolylphosphine (275 mg, 0.9 mmol) and 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (U.S. Patent Application Publication No. US 2004/0147543 Example 11, 1.5 g, 4.7 mmol). The reaction mixture was purged with nitrogen, sealed and heated at 120° C. for 24 hours. The reaction mixture was concentrated to dryness. The reaction mixture was slurried in a mixture of 1% aqueous sodium carbonate (75 mL) and chloroform (100 mL). The layers were separated. The aqueous layer was extracted with chloroform (2×25 mL). The combined organic fractions were concentrated to dryness and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-8% methanol/dichloromethane) to provide 1-{(2E)-3-[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]prop-2-enyl}pyrrolidin-2-one.

Workup

  1. customA thick walled glass tube, equipped
  2. customThe reaction mixture was purged with nitrogen
  3. customsealed
  4. concentrationThe reaction mixture was concentrated to dryness
  5. additionThe reaction mixture was slurried in a mixture of 1% aqueous sodium carbonate (75 mL) and chloroform (100 mL)
  6. customThe layers were separated
  7. extractionThe aqueous layer was extracted with chloroform (2×25 mL)
  8. concentrationThe combined organic fractions were concentrated to dryness
  9. custompurified by chromatography
  10. washa HORIZON HPFC system (silica cartridge, eluting with 0-8% methanol/dichloromethane)

Sources & evidence

ORD record
ord-1780a6e8ca94445abf9de51a261d88b3
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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