Dimethylamine → HCID 59680224, compound
Reaction equation
Cl[CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O.[CH2:21]([N:23](CC)[CH2:24]C)C.CNC.C1COCC1>C(Cl)Cl>[CH3:21][N:23]([CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])[CH3:24]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 3-Chloromethyl-2-(2-nitro-phenyl)-imidazo[1,2-a]pyridine (324 mg, 1.0 mmol) suspended in CH2Cl2 (20 ml) cooled to 0° C. was added dropwise triethylamine (303 mg, 3 eq), followed by 2 M dimethylamine in THF (8 mmol, 4 ml) in two portions over a 5 hour period. The reaction mixture was concentrated to dryness, dissolved in CH2Cl2 (20 ml) washed with water, brine, dried over Na2SO4, concentrated and purified by chromatography using a 9:1 mixture of CH2Cl2 /MeOH. The fractions were concentrated, dissolved in THF (15 ml), and stirred over H2 balloon with 10% Pd/C (10 mg) overnight. The reaction mixture was filtered through Celite and concentrated to obtain the product as a yellow solid (164 mg). (MS, M++H=267.1)
Workup
- concentrationThe reaction mixture was concentrated to dryness
- dissolutiondissolved in CH2Cl2 (20 ml)
- washwashed with water, brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- custompurified by chromatography
- additiona 9:1 mixture of CH2Cl2 /MeOH
- concentrationThe fractions were concentrated
- dissolutiondissolved in THF (15 ml)
- filtrationThe reaction mixture was filtered through Celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-87219730fa9c4c938c414341dbe46405
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093401B2
Reaction notes
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