Trifluoroacetic acid → HCID 58069237, compound

HRID 469141Notes

Reaction equation

HRID 469141 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[N:4][C:5](Cl)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[N:7]=1.[CH3:22][N:23]([CH3:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)C(O)=O>CN(C)C=O.O.C(#N)C>[NH2:1][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[N:4][C:5]([C:27]2[CH:28]=[CH:29][C:24]([N:23]([CH3:33])[CH3:22])=[CH:25][CH:26]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[N:7]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 27343444-(Dimethylamino)phenylboronic acidHCID 86661532HCID 86661532, compound

Product 1

HCID 58069237HCID 58069237, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-6-chloro-5-[4-(methylsulfonyl)phenyl]pyrazine-2-carboxylic acid (0.18 mmol, 60 mg,), 4-(dimethylamino)phenyl boronic acid (0.24 mmol, 40 mg), tetrakis(triphenylphosphine) Pd(0) (0.033 mmol, 38 mg), cesium carbonate (2.1 mmol, 297 mg) in dimethylformamide (2 ml) and deionized water (0.4 ml) was mixed under argon at room temperature. The reaction was heated in a microwave reactor at 120° C. for 15 min. The product was characterized by LC-MS (5-50 acetonitrile with 0.1% trifluoroacetic acid, positive ion [M+H]+=413).

Workup

  1. additionwas mixed under argon at room temperature

Sources & evidence

ORD record
ord-3b29573b9c2e479ebe0150e8c8ab8789
Source dataset
uspto-grants-2014_01
Patent number
US08628751B2

Reaction notes

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