Diisopropylethylamine → HCID 70921741, compound
Reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[CH3:27][O:28][CH2:29][C:30](Cl)=[O:31]>C(Cl)Cl>[CH3:27][O:28][CH2:29][C:30]([NH:15][C:11]1[CH:10]=[C:9]([O:8][C:7]2[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:14]=[CH:13][N:12]=1)=[O:31]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(4-nitrophenoxy)pyridin-2-amine [US Pat Appl 2008319188, Production Example 53] (0.60 g, 2.60 mmol) and DIPEA (0.680 μL, 3.89 mmol) in DCM (15.0 mL) under nitrogen at 0° C. was added 2-methoxyacetyl chloride (225 μL, 3.89 mmol) dropwise over 5 min. The reaction was maintained at RT for 16 hr and was quenched by the addition of a 1% solution of NH3 in MeOH (10 mL). The mixture was evaporated in vacuo and the residue was taken up into DCM (50 mL) and was washed with water (25 mL) and brine (25 mL), and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, EtOAc in DCM, 0-30%, gradient elution) to afford 2-methoxy-N-(4-(4-nitrophenoxy)pyridin-2-yl)acetamide as a white solid (0.73 g, 92%); Rt 1.88 min (Method 2); m/z 304 (M+H)+ (ES+).
Workup
- customwas quenched by the addition of a 1% solution of NH3 in MeOH (10 mL)
- customThe mixture was evaporated in vacuo
- washwas washed with water (25 mL) and brine (25 mL)
- dry with materialdried (MgSO4)
- customevaporated in vacuo
- customThe residue was purified by flash column chromatography (SiO2, EtOAc in DCM, 0-30%, gradient elution)
Sources & evidence
- ORD record
- ord-3442da9e5af541859f8b47a776c7c0aa
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299074B2
Reaction notes
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