Acetic Acid → HCID 25095102, compound

HRID 2039779Notes

Reaction equation

HRID 2039779 reaction equation
Cl.[C:2]12([CH2:12][NH:13][C:14]([C:16]3[C:17]4[N:18]([N:22]=[C:23](CC#N)[CH:24]=4)[CH:19]=[CH:20][CH:21]=3)=[O:15])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH3:28][C:29]([OH:31])=[O:30]>>[C:2]12([CH2:12][NH:13][C:14]([C:16]3[C:17]4[N:18]([N:22]=[C:23]([CH2:28][C:29]([OH:31])=[O:30])[CH:24]=4)[CH:19]=[CH:20][CH:21]=3)=[O:15])[CH2:11][CH:6]3[CH2:5][CH:4]([CH2:10][CH:8]([CH2:7]3)[CH2:9]1)[CH2:3]2

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 25095101HCID 25095101, compound

Product 1

HCID 25095102HCID 25095102, compound

Conditions

Temperature
60 °C

Procedure

A solution of conc. HCl (2.3 mL) and AcOH (4.6 mL) is added to 2-cyanomethylpyrazolo[1,5-a]pyridine-4-carboxylic acid (adamantan-1-ylmethyl)amide. The solution is warmed to 60° C. for 20 h. The volatiles are removed under reduced pressure, and the residue is dissolved in 1 M aq. NaOH (10 mL). The solution is washed with Et2O (20 mL). The aqueous layer is acidified to ˜pH 3 with 1 M aq. HCl. The mixture is filtered and the filtrate dried to afford the title compound as a light tan solid. 1H NMR (400 MHz, ((CD3)2SO) δ: 8.71 (d, 1H), 8.40 (bt, 1H), 7.60 (d, 1H), 6.90 (t, 1H), 6.79 (s, 1H), 3.75 (s, 2H), 2.99 (d, 2H), 1.88-1.96 (m, 3H), 1.46-1.70 (m, 12H). LC-MS m/z+H+): 368.3; RT=1.27 min.

Workup

  1. customThe volatiles are removed under reduced pressure
  2. dissolutionthe residue is dissolved in 1 M aq. NaOH (10 mL)
  3. washThe solution is washed with Et2O (20 mL)
  4. filtrationThe mixture is filtered
  5. customthe filtrate dried

Sources & evidence

ORD record
ord-814ba112f0d64b33bb1ed073f1795fa7
Source dataset
uspto-grants-2013_11
Patent number
US08580812B2

Reaction notes

Loading…