Triethylamine → HCID 66700028, compound

HRID 1910732Notes

Reaction equation

HRID 1910732 reaction equation
[NH2:1][CH:2]1[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][O:14][C:8]3=[CH:7][C:6]=2[N:5]([C:15](=[O:17])[CH3:16])[CH:4]([CH3:18])[CH2:3]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(N(CC)CC)C.[Cl-].[NH4+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:1][C@H:2]2[C:11]3[CH:10]=[C:9]4[O:12][CH2:13][O:14][C:8]4=[CH:7][C:6]=3[N:5]([C:15](=[O:17])[CH3:16])[C@@H:4]([CH3:18])[CH2:3]2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 742994-Chlorophenylboronic acidHCID 67491052HCID 67491052, compound

Product 1

HCID 66700028HCID 66700028, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

[Step 5] 40 mg (0.16 mmol) of the 1-(8-amino-6-methyl-7,8-dihydro-[1,3]dioxolo[4.5-g]quinolin-5(6H)-yl)ethanone, 38 mg (0.24 mmol) of 4-chlorophenylboronic acid, 59 mg (0.33 mmol) of copper (II) acetate, 49 mg (0.48 mmol) of triethylamine and 2 mL of dichloromethane suspension containing 30 mg of molecular sieve (4A) were vigorously stirred for 2 days. Following completion of the reaction, aqueous ammonium chloride solution was added followed by extraction with chloroform. The extract was washed with water and the organic layer was dehydrated with anhydrous sodium sulfate. The solution was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain 18 mg of cis-1-[8-(4-chlorophenylamino)-6-methyl-7,8-dihydro[1,3]dioxolo[4,5-g]quinolin-5(6H)-yl]ethanone in the form of a yellow oil (29%, 2 steps).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with chloroform
  3. washThe extract was washed with water
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2db3ad3cee8746a8abb6c55b12ac941c
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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