Morpholine → HCID 69311567, compound

HRID 860478Notes

Reaction equation

HRID 860478 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:14]([CH2:15][O:16][CH2:17][C:18](O)=[O:19])=[N:13][N:12]2[C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=[C:11]2[C:10]=1[C:26]1[CH:27]=[N:28][CH:29]=[C:30]([CH3:32])[CH:31]=1)[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>CN(C)C=O>[CH2:24]([C:21]1[N:12]2[N:13]=[C:14]([CH2:15][O:16][CH2:17][C:18]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[O:19])[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:33])=[C:10]([C:26]3[CH:27]=[N:28][CH:29]=[C:30]([CH3:32])[CH:31]=3)[C:11]2=[CH:23][CH:22]=1)[CH3:25]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69311658HCID 69311658, compound

Product 1

HCID 69311567HCID 69311567, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {[3-(5-ethoxy-5-oxopentyl)-7-ethyl-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazin-2-yl]methoxy}acetic acid (55 mg), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (34.9 mg) and 1-hydroxybenotriazole (24.6 mg) in dimethylformamide (2 mL) was added morpholine (12.7 mg) and the mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of ethyl acetate and methanol (50:1–20:1) to give ethyl 5-(7-ethyl-4-(5-methyl-3-pyridinyl)-2-{[2-(4-morpholinyl)-2-oxoethoxy]methyl}pyrrolo[1,2-b]pyridazin-3-yl)pentanoate as yellow oil (50 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with saturated sodium bicarbonate solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of ethyl acetate and methanol (50:1–20:1)

Sources & evidence

ORD record
ord-c1c2641b4c59428e9ba4c561b97f6cdf
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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