1-Phenethylamine → HCID 68431519, compound

HRID 2092060Notes

Reaction equation

HRID 2092060 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][CH2:10][C:11](O)=[O:12])[N:5]=[CH:4][C:3]=1[NH:14][C@@H:15]1[CH2:20][C@@H:19]2[CH2:21][C@@H:17]([C:18]2([CH3:23])[CH3:22])[C@H:16]1[CH3:24].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[C:44]1([CH:50]([NH2:52])[CH3:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][CH2:10][C:11]([NH:52][CH:50]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH3:51])=[O:12])[N:5]=[CH:4][C:3]=1[NH:14][C@@H:15]1[CH2:20][C@@H:19]2[CH2:21][C@@H:17]([C:18]2([CH3:23])[CH3:22])[C@H:16]1[CH3:24]

Participants

7

Reactant 4

HCID 74081-PhenethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68432023HCID 68432023, compound

Product 1

HCID 68431519HCID 68431519, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}propanoic acid (32 mg, 0.080 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (31 mg, 0.160 mmol), 1-hydroxybenzotriazole anhydride (11 mg, 0.080 mmol) and triethylamine (22 μL, 0.160 mmol) in N,N-dimethylformamide (1 mL) were stirred with 1-phenylethylamine (20 μL, 0.160 mmol) at room temperature for 24 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/methanol=15/1) to give the desired product (38 mg, 95% yield).

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-1910154630d44cff9a929b674d79c9a7
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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