4-Aminopyridine → HCID 53373379, compound

HRID 2409234Notes

Reaction equation

HRID 2409234 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.O1CCOCC1>O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[CH:3]=[C:2]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 312751,4-DioxaneHCID 53344728HCID 53344728, compound

Product 1

HCID 53373379HCID 53373379, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 259 mg (1.00 mmol) 4-chloro-2-(2-fluorophenyl)-[1,8]naphthyridine and 104 mg (1.10 mmol) 4-aminopyridine in 5 ml dioxane 236 mg (2.10 mmol) potassium tert.-butylate were added, the mixture heated to 80° C. and kept at this temperature for 1 hr. After cooling to ambient temperature water was added to the reaction mixture. The precipitate formed was filtered off, washed with water and dried in vacuum. This yielded [2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-4-yl-amine as beige crystals; HPLC-MS: [M+H] 317. 1H-NMR (d6-DMSO): δ [ppm]=7.34 (d, J=5.9 Hz, 2H), 7.38 (dd, J1=11.8 Hz, J2=8.2 Hz, 1H), 7.41 (t, J=7.4 Hz, 1H), 7.57 (m, 1H), 7.66 (dd, J1=8.3 Hz, J2=4.1 Hz, 1H), 7.83 (s, 1H), 8.12 (t, J=7.8 Hz, 1H), 8.46 (d, J=5.9 Hz, 2H), 8.81 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 9.1 (dd, J1=4.3 Hz, J2=1.8 Hz, 1H), 9.67 (bs, 1H).

Workup

  1. additionwere added
  2. additionwas added to the reaction mixture
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried in vacuum

Sources & evidence

ORD record
ord-17287065eaab4ee0ac8334859e311a99
Source dataset
uspto-grants-2014_08
Patent number
US08815893B2

Reaction notes

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