Sodium Carbonate → HCID 178491364, compound
Reaction equation
C(O)(=O)C.Br[C:6]1[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[O:25][CH3:26])=[NH:14])=[N:8][CH:9]=[CH:10][CH:11]=1.[C:27]1(OB(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:26][O:25][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=1[CH2:16][NH:15][C:13]([NH:12][C:7]1[C:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)=[NH:14]Participants
Conditions
- Temperature
- 110 °C
Procedure
The preparation was carried out analogously to Example 56, using 0.200 g (0.470 mmol) N-(3-bromopyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine acetate, 0.086 g (0.705 mmol) phenylboric acid, 0.149 g (1.411 mmol) sodium carbonate, and 0.038 g (0.033 mmol) tetrakis-(triphenylphosphine)palladium(0). The mixture was likewise heated in a reaction block for 20 hr at 110° C. under a nitrogen atmosphere. However, after this reaction time the starting material/product ratio was still 1:1. Therefore, further heating was performed for 16 hr, and then for an additional 25 hr. After a total reaction time of 61 hr the reaction was terminated due to increasing formation of by-products. After appropriate workup and purification via preparative HPLC, 41 mg pure N-(2,6-dimethoxybenzyl)-N′-(3-phenylpyridin-2-yl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1.2).
Workup
- temperatureTherefore, further heating
- waitfor an additional 25 hr
- customAfter a total reaction time of 61 hr the reaction was terminated due
- temperatureto increasing formation of by-products
- customAfter appropriate workup and purification via preparative HPLC
Sources & evidence
- ORD record
- ord-7de75268b4fd401aa0e0e04e912fb90f
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296697B2
Reaction notes
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