Hydrochloric Acid → HCID 10181589, compound

HRID 1373797Notes

Reaction equation

HRID 1373797 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:10]([C:11]3[CH:16]=[C:15]([CH2:17][O:18]C4CCCCO4)[N:14]=[C:13]([NH:25][CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:10]([C:11]3[N:12]=[C:13]([NH:25][CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[N:14]=[C:15]([CH2:17][OH:18])[CH:16]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86616857HCID 86616857, compound

Product 1

HCID 10181589HCID 10181589, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-6-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-pyrimidinamine (1.18 g, 2.26 mmol) in tetrahydrofuran (20 mL) at 0° C. was added hydrochloric acid (8 mL, 4 N aqueous, 32 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 48 hours. The solution was diluted and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes:ethyl acetate) provided [6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-(cyclopentylamino)-4-pyrimidinyl]methanol (815 mg, 82%) as a solid. Rf 0.21 (2:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.31 (d, 1H), 7.60 (m, 2H), 7.22 (m, 1H), 7.10 (m, 2H), 7.01 (d, 1H), 6.23 (s, 1H), 5.37 (d, 1H), 4.33 (m, 3H), 3.95 (br, 1H), 2.03 (m, 2H), 1.62 (m, 6H); 19F NMR (CDCl3) δ −112.70; MS m/z 438 (M+1).

Workup

  1. additionThe solution was diluted
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-e31c688b33dd4f60982c260eee1efda4
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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