Triethylamine → {3-[(3-Chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester

HRID 1170479Notes

Reaction equation

HRID 1170479 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[N:19]=[C:18](Cl)[S:17][N:16]=1.C(N(CC)CC)C>CS(C)=O.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:18]1[S:17][N:16]=[C:15]([Cl:14])[N:19]=1)[CH3:12])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 11309987tert-butyl N-(3-(methylamino)propyl)carbamate

Product 1

HCID 59551923{3-[(3-Chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl esterYield 69%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(3-Methylamino-propyl)-carbamic acid tert-butyl ester (7.00 g, 36.8 mmol) and 3,5-dichloro-[1,2,4]thiadiazole (4.75 g, 30.7 mmol) were dissolved in DMSO (150 mL). Finally, triethylamine (3 mL) was added and the reaction mixture was stirred at room temperature for 24 h. After this period, brine (100 mL) was poured into the reaction vessel and the mixture was transferred to a separatory funnel. The resulting layer was extracted with DCM (3×300 mL). The DCM layer was then dried over anhydrous Na2SO4. The crude product was purified using flash silica chromatography (DCM to 9:1 DCM/MeOH) to afford 6.5 g (69%) of {3-[(3-chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester as a clear oil. [M+H]+ 307.40.

Workup

  1. waitAfter this period
  2. customthe mixture was transferred to a separatory funnel
  3. extractionThe resulting layer was extracted with DCM (3×300 mL)
  4. dry with materialThe DCM layer was then dried over anhydrous Na2SO4
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-b4b36948fd554cf6a479d2bbeebc9a8d
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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