Hydrochloric Acid → 2-(4-{5-[2-(2-Fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-3-yl}-pyrazol-1-yl)-ethanol

HRID 1404304Notes

Reaction equation

HRID 1404304 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([C:24]3[CH:25]=[N:26][N:27]([CH2:29][CH2:30][O:31]C4CCCCO4)[CH:28]=3)[CH:23]=2)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.Cl>ClCCl.O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[CH:23]=[C:22]([C:24]3[CH:25]=[N:26][N:27]([CH2:29][CH2:30][OH:31])[CH:28]=3)[CH:21]=[N:20][CH:19]=2)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 673805632-(2-fluoro-phenyl)-4-(5-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-pyridin-3-yl)-[1,8]naphthyridine

Product 1

HCID 673638732-(4-{5-[2-(2-Fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-3-yl}-pyrazol-1-yl)-ethanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 219 mg (0.44 mmol) 2-(2-fluoro-phenyl)-4-(5-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-pyridin-3-yl)-[1,8]naphthyridine in 7 ml dichloromethane was treated with 0.52 ml of a 4 N solution of hydrochloric acid in dioxane. The reaction mixture was stirred for 60 minutes and the precipitate that had formed was filtered off. The residue was dissolved in water and treated with saturated sodium carbonate solution. The resulting precipitate was filtered off, washed with water and dried under vacuum yielding 2-(4-{5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-3-yl}-pyrazol-1-yl)-ethanol as colorless crystals; HPLC-MS: 1.70 min, [M+H] 412.

Workup

  1. customthe precipitate that had formed
  2. filtrationwas filtered off
  3. dissolutionThe residue was dissolved in water
  4. additiontreated with saturated sodium carbonate solution
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e109f756033644d5b7d32214306606e7
Source dataset
uspto-grants-2014_12
Patent number
US08912216B2

Reaction notes

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