Acetic Acid → HCID 135482192, compound

HRID 2211942Notes

Reaction equation

HRID 2211942 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]4[NH:18][C:19]5[C:24]([CH:25]=4)=[CH:23][CH:22]=[CH:21][CH:20]=5)=[N:13][NH:14]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.C(O)(=[O:28])C>O>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[C:17]1[C:12]1[C:11]2[C:15](=[CH:16][C:8]([C:6]3[CH:5]=[CH:4][NH:3][C:2](=[O:28])[CH:7]=3)=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 135532327HCID 135532327, compound

Product 1

HCID 135482192HCID 135482192, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the fluoropyridine (3-3, 38 mg, 0.116 mmol) in 80% acetic acid in water (13 mL) was heated at 110° C. for 10 h. The reaction mixture was concentrated in vacuo, partitioned between ethyl acetate and 0.5N-NaOH. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. Trituation of the crude solid with ethyl acetate afforded the desired intermediate (3-4); 1H NMR (500 MHz, DMSO-d6) δ 13.5 (s, 1H), 11.7 (bs, 1H), 11.6 (s, 1H), 8.28 (d, 1H, J=8.6 Hz), 7.85 (s, 1H), 7.60 (d, 1H, J=7.8 Hz), 7.55 (dd, 1H, J=8.5, 1.5 Hz), 7.50 (d, 1H, J=6.8 Hz), 7.45 (d, 1H, J=8.1 Hz), 7.16 (d, 1H, J=1.9 Hz), 7.12 (dt, 1H, J=8.1, 0.98 Hz), 7.02 (t, 1H, J=1.9 Hz), 6.69 (d, 1H, J=1.9 Hz), 6.62 (dd, 1H, J=6.8, 1.7 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and 0.5N-NaOH
  3. washThe organic layer was washed with brine
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e294b305f1674e15aaebf029f70aacc7
Source dataset
uspto-grants-2006_09
Patent number
US07101884B2

Reaction notes

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