Acetate → HCID 178491346, compound

HRID 929667Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]([NH:11][CH2:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:21][CH3:22])=[NH:10])[CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](OB(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C>>[CH3:22][O:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:13]=1[CH2:12][NH:11][C:9]([NH:8][C:4]1[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[CH:7]=[CH:6][N:5]=1)=[NH:10]

Participants

Reactant 4

HCID 175Acetate

HCID 10340Sodium Carbonate

HCID 219397714-Fluoro-phenylboric acid

HCID 178491345HCID 178491345, compound

Product 1

HCID 178491346HCID 178491346, compoundYield 55.3%

Conditions

Temperature: 110 °C

Procedure

The preparation was carried out analogously to Example 56, using 0.160 g (0.438 mmol) N-(4-bromopyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine, 0.091 g (0.657 mmol) (4-fluorophenyl)boric acid, 0.139 g (1.314 mmol) sodium carbonate, and 0.035 g (0.031 mmol) tetrakis-(triphenylphosphine)palladium(0). The mixture was likewise heated in a reaction block for 18.5 hr at 110° C. under a nitrogen atmosphere. After appropriate workup and purification via preparative HPLC, 106.5 mg (0.242 mmol, 55%) pure N-(2,6-dimethoxybenzyl)-N′-[4-(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-eebe4c1bdf42443882ababefcdcaa752
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296697B2

Reaction notes

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