Dimethylformamide → HCID 66722463, compound

HRID 1639975Notes

Reaction equation

HRID 1639975 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:11][CH2:10][C@:9]3([CH2:16][CH2:15][CH2:14][NH:13][CH2:12]3)[C:8]2=[O:17])[CH2:3][CH2:2]1.Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([N:13]2[CH2:14][CH2:15][CH2:16][C@@:9]3([C:8](=[O:17])[N:7]([CH:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)[CH2:11][CH2:10]3)[CH2:12]2)=[N:20][CH:21]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 66722220HCID 66722220, compound

Product 1

HCID 66722463HCID 66722463, compound

Conditions

Temperature
120 °C

Procedure

A mixture of (5S)-2-(tetrahydro-2H-pyran-4-yl)-2,7-diazaspiro[4.5]decan-1-one [90 mg, 0.0004 mol, this compound was prepared by using procedures analogous to those described for the synthesis of example 92, steps 1-3], 2-chloro-5-nitropyridine (69 mg, 0.00044 mol), and potassium carbonate (160 mg, 0.0012 mol) in N,N-dimethylformamide (2 mL, 0.02 mol) was stirred at 120° C. for 1.5 hours. After cooling the reaction mixture to ambient temperature, the solid was filtered off and the filtrate was concentrated in-vacuo to afford the desired product. LC-MS: 361.2 (M+H)+. The resulting residue was dissolved in methanol and to this solution was added 10% Pd on carbon and the reaction vessel was placed under a H2 (g) atmosphere and stirred at rt for 1.5 h. The catalyst was filtered off from the mixture and the filtrate was concentrated to afford the desired product in quantitative yield and was used in the next step without further purification. LC-MS: 331.2 (M+H)+.

Workup

  1. customthis compound was prepared
  2. temperatureAfter cooling the reaction mixture to ambient temperature
  3. filtrationthe solid was filtered off
  4. concentrationthe filtrate was concentrated in-vacuo

Sources & evidence

ORD record
ord-6016fcc879f34e9491dd8fe86dbb5341
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

Loading…