Water → 4-[2-(2-amino-5-iodopyridin-3-yl)-3H-benzimidazol-5-yl]morpholin-3-one
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]2=[O:15])[CH:5]=[CH:6][C:7]=1[NH2:8].[NH2:16][C:17]1[C:22]([CH:23]=O)=[CH:21][C:20]([I:25])=[CH:19][N:18]=1.S([O-])(O)=O.[Na+].O>CN(C=O)C>[NH2:16][C:17]1[C:22]([C:23]2[NH:1][C:2]3[CH:3]=[C:4]([N:9]4[CH2:14][CH2:13][O:12][CH2:11][C:10]4=[O:15])[CH:5]=[CH:6][C:7]=3[N:8]=2)=[CH:21][C:20]([I:25])=[CH:19][N:18]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
22.4 320 mg (1.544 mmol) of 4-(3,4-diaminophenyl)morpholin-3-one are dissolved in 4 ml of DMF, and 382.99 mg (1.544 mmol) of 2-amino-5-iodopyridine-3-carbaldehyde and 0.913 ml (4.633 mmol) of 38-40% sodium hydrogensulfite solution are added at room temperature. The mixture is stirred at 150° C. for 18 hours. The batch is cooled to room temperature, poured into 20 ml of water, the precipitate which deposits in the process is separated off and washed well with about 10 ml of water. The precipitate is triturated with about 25 ml of acetonitrile, and the undissolved crystals are separated off and dried, giving 4-[2-(2-amino-5-iodopyridin-3-yl)-3H-benzimidazol-5-yl]morpholin-3-one; HPLC-MS [M+H]+ 436.0.
Workup
- temperatureThe batch is cooled to room temperature
- customis separated off
- washwashed well with about 10 ml of water
- customThe precipitate is triturated with about 25 ml of acetonitrile
- customthe undissolved crystals are separated off
- customdried
Sources & evidence
- ORD record
- ord-d3f5f62f8f054c739c70504ffeb3f729
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648201B2
Reaction notes
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