2-Morpholinoethylamine → HCID 178451294, compound

HRID 1868924Notes

Reaction equation

HRID 1868924 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[C:7]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:8]([OH:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[O:79]1[CH2:84][CH2:83][N:82]([CH2:85][CH2:86][NH2:87])[CH2:81][CH2:80]1>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[OH:14][C:8]1[C:9]([CH3:12])([CH3:13])[C:10]2[C:5]([C:6](=[O:26])[C:7]=1[C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[O:16])=[CH:4][CH:3]=[C:2]([NH:87][CH2:86][CH2:85][N:82]1[CH2:83][CH2:84][O:79][CH2:80][CH2:81]1)[CH:11]=2

Participants

8

Reactant 4

HCID 4082852-MorpholinoethylamineHCID 23676156Sodium t-butoxideHCID 86595863(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthylHCID 178451288HCID 178451288, compound

Product 1

HCID 178451294HCID 178451294, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Tert-butyl 2-(7-bromo-2-hydroxy-1,1-dimethyl-4-oxo-1,4-dihydronaphthalene-3-carboxamido)acetate (125 mg, 295 μmol, Example 53A-E), palladium acetate (7 mg, 29 μmol), racemic-2,2-bis(diphenylphosphino)-1,1-binaphthyl (18 mg, 29 μmol), and sodium tert-butoxide (42 mg, 442 μmol) were added to toluene (5892 μL) followed by 2-morpholinoethylamine (77 μL, 589 μmol). The reaction was then stirred at 110° C. for 3 hours. The reaction mixture was diluted with 100 mL of EtOAc, washed 2 times with 50 mL of 3 N HCl (aqueous), and separated. The organic layer was dried over sodium sulfate and concentrated to give crude product which was purified via HPLC to give the title compound.

Workup

  1. washwashed 2 times with 50 mL of 3 N HCl (aqueous)
  2. customseparated
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified via HPLC

Sources & evidence

ORD record
ord-fadf44d5409d408c8f507777bbbc122a
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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