Nitrogen → Pyridin-2-yl-carbamic acid 2-[5-(2-chloro-5-methoxy-phenoxy)-6-(5-isopropyl-pyridin-2-ylsulphonylamino)-pyrimidin-4-yloxy]-ethyl ester
Reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:3]=1[O:4][C:5]1[C:6]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][N:20]=2)(=[O:18])=[O:17])=[N:7][CH:8]=[N:9][C:10]=1[O:11][CH2:12][CH2:13][OH:14].[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1C(N=[N+]=[N-])=O.[N:45]#N.[O:47]1[CH2:52]COCC1>>[Cl:1][C:2]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:3]=1[O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][O:14][C:52](=[O:47])[NH:45][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=2)=[N:9][CH:8]=[N:7][C:6]=1[NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][N:20]=1)(=[O:18])=[O:17]Participants
5
Reactant 4
Product 1
Conditions
- Temperature
- 95 °C
Procedure
100 mg of N-[5-(2-chloro-5-methoxy-phenoxy)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-5-isopropyl-pyridine-2-sulphonamide and 38.5 mg of 2-pyridyl-carboxylic acid azide were dissolved in 1 ml of dry dioxan. The solution was stirred at 95° C. for 2 hours, whereby N2 was liberated. After distillation of the solvent the compound was crystallized from ethanol. 115 mg of pyridin-2-yl-carbamic acid 2-[5-(2-chloro-5-methoxy-phenoxy)-6-(5-isopropyl-pyridin-2-ylsulphonylamino)-pyrimidin-4-yloxy]-ethyl ester were obtained as white crystals with m.p. 190°-191° C.
Workup
- distillationAfter distillation of the solvent the compound
- customwas crystallized from ethanol
Sources & evidence
- ORD record
- ord-7fa4fae288274be49a4a6fa9a5439110
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05837708
Reaction notes
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