6-Methoxy-3-pyridinylamine → HCID 23589559, compound

HRID 1295757Notes

Reaction equation

HRID 1295757 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][CH3:25])=[C:8]2[N:13]([CH:14]=1)[N:12]=[CH:11][N:10]=[C:9]2NC1C=CC(C)=C(O)C=1)=[O:5])[CH3:2].[NH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[N:31][CH:32]=1>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][CH3:25])=[C:8]2[N:13]([CH:14]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:26][C:27]1[CH:32]=[N:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 811216-Methoxy-3-pyridinylamineHCID 23589558HCID 23589558, compound

Product 1

HCID 23589559HCID 23589559, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound G of Example 96 (0.1 mmol) and 5-amino-2-methoxypyridine (62 mg, 0.5 mmol) in CH3CN (0.5 mL) was stirred for 2 hrs. The crude mixture was purified by preparative HPLC. The desired material was collected, concentrated, and neutralized with aqueous NaHCO3. The solid was collected, washed with water, and dried to provide 12.5 mg (36%) of red solid. MS: [M+H]+=344; 1H NMR (CDCl3): δ 8.30 (s, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.78 (d, J=7.9 Hz, 2H), 6.77 (d, J=8.8 Hz, 1H), 4.30 (q, J=7.0 Hz, 2H), 4.11 (s, 3H), 3.89 (s, 3H), 1.33 (t, J=7.0 Hz, 3H).

Workup

  1. customThe crude mixture was purified by preparative HPLC
  2. customThe desired material was collected
  3. concentrationconcentrated
  4. customThe solid was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-cddaf4b8dd7b453da51bb689b63193b0
Source dataset
uspto-grants-2007_07
Patent number
US07244733B2

Reaction notes

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