Trifluoroacetic acid → 5-(4-Fluorophenyl)-2-({6-[(methylamino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

HRID 385776Notes

Reaction equation

HRID 385776 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[S:18][C:19]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:20][C:21]=2[C:22]([NH2:24])=[O:23])[N:11]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:19]2[S:18][C:17]([NH:16][C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:7][CH3:6])[N:11]=3)=[C:21]([C:22]([NH2:24])=[O:23])[CH:20]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59525661tert-Butyl[(6-{[3-(aminocarbonyl)-5-(4-fluorophenyl)-2-thienyl]amino}pyridin-2-yl)methyl]methylcarbamate

Product 1

HCID 251261625-(4-Fluorophenyl)-2-({6-[(methylamino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[(6-{[3-(aminocarbonyl)-5-(4-fluorophenyl)-2-thienyl]amino}pyridin-2-yl)methyl]methylcarbamate (90 mg, 0.197 mmol) in dichloromethane (0.4 mL) was added trifluoroacetic acid (0.4 mL) and the reaction was maintained at room temperature for 1 hour. The volatiles were removed in vacuo and the crude product was purified by reverse phase HPLC (20-90% acetonitrile/water with 0.05% trifluoroacetic acid). The appropriate fractions were diluted with ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (40 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (40 mL) and water (2×40 mL), dried over sodium sulfate, filtered and concentrated to yield the title compound.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe crude product was purified by reverse phase HPLC (20-90% acetonitrile/water with 0.05% trifluoroacetic acid)
  3. additionThe appropriate fractions were diluted with ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (40 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with saturated aqueous sodium bicarbonate (40 mL) and water (2×40 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-03c2f1ac3eee4d9e95faa0a7079af875
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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