Dimethylformamide → HCID 66722265, compound

HRID 1044356Notes

Reaction equation

HRID 1044356 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:13][CH2:12][C@:11]2([CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[C:10]1=[O:19].Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([N:15]2[CH2:16][CH2:17][CH2:18][C@@:11]3([C:10](=[O:19])[N:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[Cl:2])[CH2:13][CH2:12]3)[CH2:14]2)=[N:22][CH:23]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 66722410HCID 66722410, compound

Product 1

HCID 66722265HCID 66722265, compound

Conditions

Temperature
120 °C

Procedure

A mixture of (5S)-2-(2-chlorophenyl)-2,7-diazaspiro[4.5]decan-1-one hydrochloride (40.0 mg, 0.000133 mol, prepared by using a procedure analogous to that used for the synthesis of example 92, steps 1-3), 2-chloro-5-nitropyridine (23 mg, 0.00015 mol), and potassium carbonate (55 mg, 0.00040 mol) in N,N-dimethylformamide (1.0 mL, 0.013 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: 387.1 (M+H)+. The resulting residue was dissolved in methanol and to this solution was added platinum [5 wt. % (dry basis) on activated carbon, wet, Degussa type F101, RA/W (Aldrich #330159), 15 mg] under an atmosphere of H2 (g) at rt for 2 h. The catalyst was filtered off from the mixture and the filtrate was concentrated in-vacuo to afford the product in quantitative yield. LC-MS: 357.1 (M+H)+.

Workup

  1. customprepared
  2. temperatureAfter cooling the reaction mixture to ambient temperature the solid
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated in-vacuo

Sources & evidence

ORD record
ord-197c8f5c53af49acb6814f19b6071765
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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