Chloroform → HCID 58955130, compound

HRID 1992524Notes

Reaction equation

HRID 1992524 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15](OS(C)(=O)=O)[CH2:14]1.[H-].[Na+].[SH:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].C(Cl)(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15]([S:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:14]1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 24758Sodium hydrideHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 58955142HCID 58955142, compound

Product 1

HCID 58955130HCID 58955130, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methanesulfonic acid 1-(6-methoxy-[1,5]naphthyridin-4-yl)-pyrrolidin-3-yl ester (650 mg, 2 mmol, prepared as Example 2b) in DMF (3 mL) was added NaH (89 mg, 2.2 mmol, 65% in mineral oil) followed by 1,1-dimethylethyl (2-mercaptoethyl)carbamate (0.373 mL, 2.2 mmol). The resulting mixture was stirred at 25° C. for 12 h and then diluted with brine. Chloroform was used the extracted the aqueous solution. The organic fractions were pooled, concentrated and purified with column chromatography (silica, 10% MeOH in CDCl3 (1% NH4OH)) to afford the title compound as an off-white solid (630 mg, 78%): LC/MS m/z 405 (M+H)+.

Workup

  1. extractionextracted the aqueous solution
  2. concentrationconcentrated
  3. custompurified with column chromatography (silica, 10% MeOH in CDCl3 (1% NH4OH))

Sources & evidence

ORD record
ord-6dbfca886990412b8cfef29819389cab
Source dataset
uspto-grants-2010_01
Patent number
US07648984B2

Reaction notes

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