Hydrochloric Acid → HCID 89618674, compound

HRID 1476779Notes

Reaction equation

HRID 1476779 reaction equation
O[Li].O.[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([O:30]CC)=[O:29])=[C:21]2[CH:20]=1)[CH3:5].Cl>C(O)C.O>[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[C:21]2[CH:20]=1)[CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 89618660HCID 89618660, compound

Product 1

HCID 89618674HCID 89618674, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1M aq. solution of LiOH.H2O (0.4 mL) was added to a stirred solution of (R)-ethyl 5-(2-(2-ethoxy-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (Int-77) (0.12 g, 0.32 mmol) in ethanol (5 mL) and the stirring was continued at 90° C. for 8 h. The reaction mixture was concentrated under reduced pressure to afford the crude, which was diluted with cold water (20 mL) and acidified with 2N HCl solution to pH=2, solid precipitated out was filtered and dried to afford the desired compound (Int-78) as yellow solid. MS (ESI): m/z 370.3 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude, which
  3. customprecipitated out
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-b0c98fa8a89846a2823b60ffdc427521
Source dataset
uspto-grants-2016_08
Patent number
US09402833B2

Reaction notes

Loading…