Trifluoroacetic acid → 3-Amino-5-(5-fluoropyridin-2-yl)thiophene-2-carboxylic acid methyl ester

HRID 72199Notes

Reaction equation

HRID 72199 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=2)=[CH:8][C:9]=1[NH:10]C(OC(C)(C)C)=O)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=2)=[CH:8][C:9]=1[NH2:10])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689429283-tert-Butoxycarbonylamino-5-(5-fluoropyridin-2-yl)thiophene-2-carboxylic acid methyl ester

Product 1

HCID 689420543-Amino-5-(5-fluoropyridin-2-yl)thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-tert-butoxycarbonylamino-5-(5-fluoropyridin-2-yl)-thiophene-2-carboxylic acid methyl ester (80 mg) in dichloromethane (1.35 mL) was mixed with trifluoroacetic acid (0.15 mL) and stirred at room temperature overnight. The solvent was then removed in vacuo, and the residue was taken up again in dichloromethane and washed twice with saturated NaHCO3 solution and once with water. The dichloromethane phase was dried over sodium sulfate and concentrated. The product with the molecular weight of 252.27 (C11H9FN2O2S) was obtained in this way; MS (ESI): 253 (M+H+).

Workup

  1. customThe solvent was then removed in vacuo
  2. washwashed twice with saturated NaHCO3 solution and once with water
  3. dry with materialThe dichloromethane phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product with the molecular weight of 252.27 (C11H9FN2O2S) was obtained in this way

Sources & evidence

ORD record
ord-8eb6000f04664cc7b29ae986b959446c
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

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