Triethylamine → HCID 86597476, compound

HRID 860468Notes

Reaction equation

HRID 860468 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:11]=[C:12]([CH2:23][OH:24])[C:13]=2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:11]=[C:12]([CH2:23][O:24][S:38]([CH3:37])(=[O:40])=[O:39])[C:13]=2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68802719HCID 68802719, compound

Product 1

HCID 86597476HCID 86597476, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-[4-(5-bromo-3-pyridinyl)-7-ethyl-2-(hydroxymethyl)pyrrolo[1,2-b]pyridazin-3-yl]pentanoate (200 mg) and triethylamine (65.9 mg) in dichloromethane (2 mL) was added methanesulfonyl chloride (54.7 mg) under an ice-bath. After stirring for 1 hour, the reaction was quenched by adding 1N hydrochloric acid (1 mL). The mixrure was partitioned between ethyl acetate (20 mL) and 1N hydrochloric acid (5 mL). The organic layer was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated to give ethyl 5-(4-(5-bromo-3-pyridinyl)-7-ethyl-2-{[(methylsulfonyl)oxy]methyl}pyrrolo[1,2-b]pyridazin-3-yl)pentanoate as an yellow gum (247 mg).

Workup

  1. customthe reaction was quenched
  2. additionby adding 1N hydrochloric acid (1 mL)
  3. customThe mixrure was partitioned between ethyl acetate (20 mL) and 1N hydrochloric acid (5 mL)
  4. washThe organic layer was washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ce4f32a315bb40b2ac9c56cc9e865fc1
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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