3-Pyridinemethanamine → HCID 21081503, compound

HRID 2117154Notes

Reaction equation

HRID 2117154 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:25]([NH:27][C:28](=[O:37])[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[C:17]([C:18](=[O:23])C(Cl)(Cl)Cl)[C:10]=12.[NH2:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1>CN(C=O)C>[N:42]1[CH:43]=[CH:44][CH:45]=[C:40]([CH2:39][NH:38][C:18]([C:17]2[C:10]3[C:11](=[N:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]3[CH:6]=[CH:5][C:4]([NH:24][C:25]([NH:27][C:28](=[O:37])[CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)=[O:26])=[CH:3][C:2]=3[F:1])[NH:15][CH:16]=2)=[O:23])[CH:41]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 21081470HCID 21081470, compound

Product 1

HCID 21081503HCID 21081503, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-fluoro-4-(3-(2,2,2-trichloroacetyl)-1H-pyrrolo[2,3-b]pyridine 4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)urea (7.0 mg, 0.012 mmol, Example 270) in 0.5 mL of DMF was added 3-(aminomethyl)pyridine (10 mg, 0.092 mmol, Aldrich). The reaction mixture was stirred at rt for 1 h, and quenched by the addition of 1 mL of cold water. The precipitate that formed was collected by filtration, washed with cold water (1 mL) and cold acetonitrile (1 mL) and dried under vacuum to afford the desired product (4.3 mg, 64%) as a white solid. 1H NMR (DMSO-d6) δ 12.38 (s, 1H), 11.03 (s, 1H), 10.57 (s, 1H), 8.48 (s, 1H), 8.40 (t, 1H, J=5.5 Hz), 8.34 (d, 1H, J=3.3 Hz), 8.11 (d, 1H, J=5.5 Hz), 8.00 (s, 1H), 7.73 (d, 1H, J=13.2 Hz), 7.65 (d, 1H, J=7.7 Hz), 7.37-7.29 (m, 4H), 7.16 (t, 3H, J=8.8 Hz), 6.34 (d, 1H, J=5.5 Hz), 4.48 (d, 2H, J=5.5 Hz), 3.74 (s, 2H); MS(ESI+) m/z 567.1 (M+H)+.

Workup

  1. customquenched by the addition of 1 mL of cold water
  2. customThe precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with cold water (1 mL) and cold acetonitrile (1 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1626173274574a1993c0a539d3da0efa
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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