Potassium Carbonate → HCID 89851613, compound

HRID 1746905Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2=[N:14][NH:15][CH:16]=[C:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:18]1[N:28]=[CH:27][CH:26]=[CH:25][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2=[N:14][N:15]([C:18]3[N:28]=[CH:27][CH:26]=[CH:25][C:19]=3[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=[C:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

The mixture of 5-benzyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine (1.0 g, 4.69 mmol), ethyl 2-chloronicotinate (1.55 g, 8.35 mmol), K2CO3 (1.7 g, 12.30 mmol), 18-CROWN-6 (0.2 g, 0.757 mmol) and KI (0.13 g, 0.783 mmol) in N,N-dimethylformamide (15 mL) was heated to 140° C. under stirring. After completion of the reaction the mixture was concentrated, the remainder dissolved in 250 mL of dichloromethane, washed subsequently with water (3×30 mL) and brine, dried (MgSO4), filtered and concentrated to give 2.21 g of a brown oil, which was purified by chromatography over silica gel (eluent CH2Cl2/methanol). 200 mg of the title compound was obtained as a white amorphous solid; ESI-MS [M+H]+: 363.2.

Workup

customAfter completion of the reaction the mixture
concentrationwas concentrated
dissolutionthe remainder dissolved in 250 mL of dichloromethane
washwashed subsequently with water (3×30 mL) and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d4ad060007c445e28c1c44bf96cf5c7b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150545B2

Reaction notes

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