Hydrochloric Acid → HCID 67252265, compound

HRID 2042061Notes

Reaction equation

HRID 2042061 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([N:20](CC)[CH2:21][C:22]3C=CC(OC)=CC=3)[CH:15]=2)=[CH:11][C:10]=1[F:34].Cl.O>C(Cl)Cl>[NH2:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][CH3:22])[CH:15]=2)=[CH:11][C:10]=1[F:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6422Trifluoroacetic acidHCID 67253189HCID 67253189, compound

Product 1

HCID 67252265HCID 67252265, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Trifluoroacetic acid (10 mL) was added to a solution of [4-(4-amino-3-fluoro-phenoxy)-pyridin-2-yl]-ethyl-(4-methoxybenzyl)amine (1.2 g, 3.27 mmol) in CH2Cl2 (50 mL) and the resulting solution was heated to 40° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was treated with HCl (5 mL, 12M, 60 mmol) and water (50 mL). The solution was washed with EtOAc (4×50 mL). The aqueous layer was treated with NaHCO3 until pH=8 and then extracted with EtOAc (3×50 mL). The combined extracts were washed with brine (3×50 mL), dried (NaSO4) and concentrated in vacuo to give 4-(4-amino-3-fluorophenoxy)-N-ethylpyridin-2-amine (0.45 g, 67% yield). 1H NMR (300 MHz, DMSO-d6) δ7.79 (d, J=5.7, 1H), 6.85 (dd, J=11.7, 2.4 Hz, 1H), 6.78 (t, J=8.7 Hz, 1H), 6.67 (dd, J=8.7, 2.4 Hz, 1H), 6.39 (m, 1H), 6.05 (dd, J=5.7, 2.1 Hz, 1H), 5.72 (d, J=2.1 Hz, 1H), 5.09 (s, 2H), 3.15 (m, 2H), 1.03 (t, J=7.2, 3H); MS (ESI) m/z: 248.2 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washThe solution was washed with EtOAc (4×50 mL)
  3. additionThe aqueous layer was treated with NaHCO3 until pH=8
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined extracts were washed with brine (3×50 mL)
  6. dry with materialdried (NaSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-940ac7f354094d41b540e9532e79f129
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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