Trifluoroacetic acid → 4'-[(2-Aminoethyl)oxy]-2'-methyl-3-biphenylcarboxamide trifluoroacetate

HRID 70317

Reaction equation

HRID 70317 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)=[CH:12][C:11]=2[CH3:27])[CH:7]=[CH:8][CH:9]=1)=[O:3].[SiH](CC)(CC)CC.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[NH2:19][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:2]([NH2:1])=[O:3])[CH:5]=2)=[C:11]([CH3:27])[CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 593163811,1-Dimethylethyl (2-{[3'-(aminocarbonyl)-2-methyl-4-biphenylyl]oxy}ethyl)carbamate

Product 1

HCID 671602804'-[(2-Aminoethyl)oxy]-2'-methyl-3-biphenylcarboxamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (2-{[3′-(aminocarbonyl)-2-methyl-4-biphenylyl]oxy}ethyl)carbamate (0.090 g; 0.24 mmol; I-VII-2) and Et3SiH (0.1 mL; 0.6 mmol) in CH2Cl2 (5 mL) at room temperature was added TFA (1 mL) in one portion. The mixture was aged 2 h and concentrated in vacuo, affording the title compound as a pale yellow gum which was used without further purification. LC/MS (method A) 1.18 min, m/z 271 (M+H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21c5ec7b0379432c95bbb6da415a0510
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Linked notes

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