Morpholine → HCID 68430769, compound

HRID 2092057Notes

Reaction equation

HRID 2092057 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10](O)=[O:11])[N:5]=[CH:4][C:3]=1[NH:13][C@@H:14]1[CH2:19][C@@H:18]2[CH2:20][C@@H:16]([C:17]2([CH3:22])[CH3:21])[C@H:15]1[CH3:23].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:13][C@@H:14]1[CH2:19][C@@H:18]2[CH2:20][C@@H:16]([C:17]2([CH3:21])[CH3:22])[C@H:15]1[CH3:23]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68431388HCID 68431388, compound

Product 1

HCID 68430769HCID 68430769, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}acetic acid (30 mg, 0.078 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (22 mg, 0.117 mmol), 1-hydroxybenzotriazole anhydride (16 mg, 0.117 mmol) and triethylamine (16 μL, 0.117 mmol) in N,N-dimethylformamide (0.3 mL) was stirred with morpholine (10 μL, 0.117 mmol) at room temperature for 5 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium sulfate and saturated aqueous sodium hydrogen carbonate 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/ethyl acetate=1/1) to give the desired product (20 mg, 57% yield).

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous ammonium sulfate and saturated aqueous sodium hydrogen carbonate 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/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-cf4055c24d404d03825df71f30fce71a
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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