Acetate → HCID 178491365, compound

HRID 929671Notes

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.[F:27][C:28]1[CH:33]=[CH:32][C:31](OB(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C>>[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:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)=[NH:14]

Participants

Reactant 4

HCID 175Acetate

HCID 10340Sodium Carbonate

HCID 219397714-Fluoro-phenylboric acid

HCID 178476656HCID 178476656, compound

Product 1

HCID 178491365HCID 178491365, compoundYield 31.3%

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, 0.099 g (0.705 mmol) (4-fluorophenyl)boric 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 24 hr at 110° C. under a nitrogen atmosphere. After appropriate workup and purification via preparative HPLC, 65 mg (0.147 mmol, 31%) pure N-(2,6-dimethoxybenzyl)-N′-[3-(4-fluorophenyl)pyridin-2-yl]guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1).

Workup

customAfter appropriate workup and purification via preparative HPLC

Sources & evidence

ORD record: ord-20c125f53bc640909b57132422713990
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296697B2

Reaction notes

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