Ethanolamine → HCID 69309298, compound

HRID 2250631Notes

Reaction equation

HRID 2250631 reaction equation
[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]([CH3:22])[C:10]([C:19]([OH:21])=O)=[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)[C:6]2=[CH:5][CH:4]=1)[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[NH2:35][CH2:36][CH2:37][OH:38]>CN(C)C=O>[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]([CH3:22])[C:10]([C:19]([NH:35][CH2:36][CH2:37][OH:38])=[O:21])=[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)[C:6]2=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68804452HCID 68804452, compound

Product 1

HCID 69309298HCID 69309298, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-ethyl-2-methyl-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazine-3-carboxylic acid (70 mg), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (68.2 mg) and 1-hydroxybenotriazole (48 mg) in dimethylformamide (2 mL) was added 2-aminoethanol (17.4 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 chloroform and methanol (50:1-10:1). The crude product was triturated with isopropylether to give 7-ethyl-N-(2-hydroxyethyl)-2-methyl-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazine-3-carboxamide as a yellow powder (47 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 chloroform and methanol (50:1-10:1)
  8. customThe crude product was triturated with isopropylether

Sources & evidence

ORD record
ord-768bb9794ffb47818e653385ba0a159c
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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