Benzenemethanamine, 3,4-dichloro- → HCID 59168050, compound
Reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])[C:5]([N+:15]([O-])=O)=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:31][NH2:32].[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.CCOC(C)=O>[NH2:15][C:5]1[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[N:7][C:2]([NH:32][CH2:31][C:30]2[CH:33]=[CH:34][C:35]([Cl:36])=[C:28]([Cl:27])[CH:29]=2)=[N:3][CH:4]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
To a suspension of N-(2-(2-chloro-5-nitropyrimidin-4-ylamino)ethyl)acetamide as prepared in Example 1A (100 mg, 0.39 mmol) in THF (5 mL) was added 80 μL of N,N-diisopropylethylamine followed by of 3,4-dichlorobenzylamine. The mixture was stirred at 60° C. for 16 hours. The mixture was then diluted with 5 mL of THF and a solution of 0.6 g of Na2S2O4 (85% tech. grade, 2.9 mmol) and 0.9 g of Na2CO3 (8.5 mmol) in 10 mL of water was added. The mixture was stirred at 60° C. for 10 h and allowed to cool to room temperature. The mixture was diluted with 30 mL of EtOAc and washed with 20 mL of saturated NaHCO3 solution and 20 mL of brine. The combined organic phase was dried over MgSO4 and concentrated to provide crude N-{2-[(5-amino-2-{[(3,4-dichlorophenyl)methyl]amino}pyrimidin-4-yl)amino]ethyl}acetamide which was used the without further purification. m/z (ESI) found 369.2 [M+H+].
Workup
- stirringThe mixture was stirred at 60° C. for 10 h
- temperatureto cool to room temperature
- washwashed with 20 mL of saturated NaHCO3 solution and 20 mL of brine
- dry with materialThe combined organic phase was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-31ac12ea7a844a4eb728b1bd60b15ca7
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662819B2
Reaction notes
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