Morpholine → HCID 69308860, compound

HRID 860471Notes

Reaction equation

HRID 860471 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=3)[N:12]=[C:13]([CH3:22])[C:14]=2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>CN(C)C=O>[CH2:26]([C:23]1[N:11]2[N:12]=[C:13]([CH3:22])[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([N:50]3[CH2:55][CH2:54][O:53][CH2:52][CH2:51]3)=[O:21])=[C:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[C:1]#[N:2])[C:10]2=[CH:25][CH:24]=1)[CH3:27]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68802396HCID 68802396, compound

Product 1

HCID 69308860HCID 69308860, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoic acid (50 mg) in N,N-dimethylformamide (1 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35 mg) and 1-hydroxybenzotriazole (28 mg) at ambient temperature. After 30 minutes, to the mixture was added morpholine (24 mg). After 5 hours, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with water three times and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by flash silica gel column chromatography (silica gel, 40 mL) eluted with hexane-ethyl acetate=3-1, 2-1, 1-1, 1-3, and 0-1 to give 3-{7-ethyl-2-methyl-3-[5-(4-morpholinyl)-5-oxopentyl]pyrrolo[1,2-b]pyridazin-4-yl}benzonitrile as an yellow gum (53 mg)

Workup

  1. waitAfter 5 hours
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic layer was washed with water three times and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash silica gel column chromatography (silica gel, 40 mL)
  7. washeluted with hexane-ethyl acetate=3-1, 2-1, 1-1, 1-3, and 0-1

Sources & evidence

ORD record
ord-1be266a9a61141dba5711df2129fe2ed
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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