Ethyl bromoacetate → HCID 70823496, compound

HRID 2092111Notes

Reaction equation

[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[OH:20])=[O:11])[N:5]=[CH:4][C:3]=1[NH:21][C@@H:22]1[CH2:27][C@@H:26]2[CH2:28][C@@H:24]([C:25]2([CH3:30])[CH3:29])[C@H:23]1[CH3:31].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CC(C)=O>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][O:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:10](=[O:11])[CH2:9][N:6]1[C:7](=[O:8])[C:2]([Cl:1])=[C:3]([NH:21][C@@H:22]2[CH2:27][C@@H:26]3[CH2:28][C@@H:24]([C:25]3([CH3:30])[CH3:29])[C@H:23]2[CH3:31])[CH:4]=[N:5]1)[CH3:38]

Participants

Conditions

Temperature: 50 °C

Procedure

2-[5-Chloro-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl]-N-[(3-hydroxypyridin-4-yl)methyl]acetamide (12.7 mg, 0.03 mmol) in acetone (2 mL) was mixed with ethyl bromoacetate (4.4 μL, 0.04 mmol) and potassium carbonate (5.9 mg, 0.04 mmol) at room temperature and stirred at 50° C. for 1 hour. After cooling, the reaction solution was mixed with saturated aqueous ammonium chloride and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1) to give the desired product (4.8 mg, 30%).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1)

Sources & evidence

ORD record: ord-6141e45ac93b42f9887c68f7a8ea3b7d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440666B2

Reaction notes

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