Ammonium formate → HCID 178419835, compound

HRID 2204639Notes

Reaction equation

HRID 2204639 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:22]3=[C:23]4[CH:29]=[CH:28][NH:27][C:24]4=[N:25][CH:26]=[C:21]3[NH:20][N:19]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:22]3=[C:23]4[CH:29]=[CH:28][NH:27][C:24]4=[N:25][CH:26]=[C:21]3[NH:20][N:19]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178420309HCID 178420309, compound

Product 1

HCID 178419835HCID 178419835, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Ammonium formate (0.50 g, 7.9 mmol) and Pearlman's catalyst (0.56 g, 0.79 mmol) were added to a solution of 1-(1-benzylpiperidin-4-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine (0.26 g, 0.791 mmol, Example #24) in MeOH (20 mL). The reaction was heated at about 65° C. for about 1 h then filtered through Celite® and concentrated under reduced pressure. The filtrate was concentrated to afford 1-(piperidin-4-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine (0.161 g, 84%): LC/MS (Table 2, Method a)Rt=1.18 min; MS m/z: 242 (M+H)+, 240 (M−H)−. The crude product was used directly in subsequent steps without further purification.

Workup

  1. filtrationthen filtered through Celite®
  2. concentrationconcentrated under reduced pressure
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4064bf46c1f340889b51e32d612d6dd6
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

Loading…