Sodium Carbonate → [8-(3-Aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-(3,5-dimethoxy-phenyl)-amine

HRID 570603Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.[NH2:22][CH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:22][CH2:23][C:24]1[CH:29]=[C:28]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH:11][C:12]4[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=4)[N:10]=3)[CH:5]=[CH:6][N:7]=2)[CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (8-chloro-[1,2,4]triazolo[1,5-a]pyrazine-2-yl]-(3,5-dimethoxy-phenyl)-amine (0.2 g, 0.65 mmol, 1 eq) in a mixture of dimethoxy ethane (3 ml) and water (1 ml), 3-aminomethylphenyl boronic acid (0.28 g, 1.31 mmol, 2 eq), sodium carbonate (0.14 g, 1.31 mmol, 2 eq)) and dichlorobis(triphenyl-phospine)palladium (II) (0.023 g, 0.03 mmol, 5%) are taken in a microwave vial and heated at 120° C. for 2 hours. The reaction mixture is concentrated and the residue is taken in dichloromethane (10 ml×1), washed with brine solution (10 ml×1), the organic layer is dried over anhydrous MgSO4 and concentrated. The crude product obtained is purified by silica gel column using (230-400) mesh to get the titled product as yellow solid.

Workup

concentrationThe reaction mixture is concentrated
washwashed with brine solution (10 ml×1)
dry with materialthe organic layer is dried over anhydrous MgSO4
concentrationconcentrated
customThe crude product obtained
customis purified by silica gel column

Sources & evidence

ORD record: ord-b6dec6b7854a4deab300a40132862a9f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023851B2

Reaction notes

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