Potassium Hydroxide → HCID 59539009, compound

HRID 2039776Notes

Reaction equation

HRID 2039776 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:30]=[C:11]2[C:12]([C:16](=[O:29])[NH:17][CH2:18][C:19]34[CH2:28][CH:23]5[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]5)[CH2:20]3)[CH2:26]4)=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1)=[O:7])C>CCO>[C:19]12([CH2:18][NH:17][C:16]([C:12]3[C:11]4[N:10]([N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:30]=4)[CH:15]=[CH:14][CH:13]=3)=[O:29])[CH2:28][CH:23]3[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]3)[CH2:26]1)[CH2:20]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 25094826HCID 25094826, compound

Product 1

HCID 59539009HCID 59539009, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 M Aqueous KOH (2.6 mL) is added to a mixture of 4-[(adamantan-1-ylmethyl)carbamoyl]-pyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester (503 mg, 1.32 mmol) and EtOH (6.6 mL). After 4 h, the volatiles are removed under reduced pressure. The aqueous residue is diluted with water (2 mL) and then acidified with 1 M aq. HCl to ˜pH 2. The solids are collected by filtration and then dried to afford the title compound as a light yellow powder. 1H NMR (400 MHz, ((CD3)2SO) δ: 8.86 (d, 1H), 8.50 (t, 1H), 7.71 (d, 1H), 7.26 (s, 1H), 7.12 (t, 1H), 3.00 (d, 2H), 1.88-1.98 (m, 3H), 1.48-1.69 (m, 12H). LC-MS m/z (M+H+): 354.09.

Workup

  1. customthe volatiles are removed under reduced pressure
  2. additionThe aqueous residue is diluted with water (2 mL)
  3. filtrationThe solids are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-3a9591ae0381482cbf1c49484019dc24
Source dataset
uspto-grants-2013_11
Patent number
US08580812B2

Reaction notes

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