Hydrochloric Acid → HCID 178427845, compound

HRID 2250052Notes

Reaction equation

HRID 2250052 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].CCN(CC)CC.NCCS(O)(=O)=[O:43].Cl>CN1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([OH:43])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1123TaurineHCID 8471TriethylamineHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 178427845HCID 178427845, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

To a solution of 8-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one (223 mg, 0.5 mmol) in N-methylpyrollidine (5 mL) was added Et3N (0.1 mL) followed by 2-aminoethanesulfonic acid (200 mg, 1.5 mmol, 3 eq) and the reaction mixture was heated to 50° for 12 h. 1 M aq HCl was then added dropwise till pH 3. The reaction mixture was then extracted with EtOAc (2×20 mL). Organic layers were combined, washed with satd aq NaCl, dried (MgSO4), filtered and solvent was evaporated. The yellow residue was then purified by flash chromatography to give an oily product, which was then recrystalized from methanol:H2O (3:1) to afford 51 mg of pure 8-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-hydroxy-8H-pyrido[2,3-d]pyrimidin-7-one. 1H-NMR (CDCl3): δ 2.24 (s, 3H), 6.31 (d, 1H, J=9.8 Hz), 7.02 (m, 5H). 7.23 (m, 1H), 7.352 (m, 1H), LC MS (m/e)=384.2 (MH+). Rt=1.65 min.

Workup

  1. temperaturethe reaction mixture was heated to 50° for 12 h
  2. extractionThe reaction mixture was then extracted with EtOAc (2×20 mL)
  3. washwashed with satd aq NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customsolvent was evaporated
  7. customThe yellow residue was then purified by flash chromatography
  8. customto give an oily product, which
  9. customwas then recrystalized from methanol:H2O (3:1)

Sources & evidence

ORD record
ord-fdea2852276f4ceaa65cd85295c62ac8
Source dataset
uspto-grants-2008_01
Patent number
US07314934B2

Reaction notes

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