Triethylamine → (4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

HRID 1717321Notes

Reaction equation

HRID 1717321 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)[C:11]=2[CH2:12][OH:13])=[O:6])[CH2:3][CH2:2]1.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH3:28][S:25]([O:13][CH2:12][C:11]1[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)[N:9]=[N:8][C:7]=1[C:5]([NH:4][CH:1]1[CH2:2][CH2:3]1)=[O:6])(=[O:27])=[O:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57665224N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 86629804(4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonateYield 94.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide (1.12 g, 3.39 mmol) obtained in Example 112 and mesyl chloride (0.293 ml, 3.73 mmol, 1.1 eq.) were dissolved in THF (22 ml), and a solution of triethylamine (0.615 ml, 4.41 mmol, 1.3 eq.) in THF (2 ml) was added dropwise over 10 min with stirring at 0° C. The reaction mixture was stirred at 0° C. for 50 min. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with 10% brine and saturated brine. The aqueous layers were each extracted with ethyl acetate (50 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated. Diethyl ether was added and the precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (1.31 g, 3.21 mmol, 94.6%).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 50 min
  2. washwashed with 10% brine and saturated brine
  3. extractioneach extracted with ethyl acetate (50 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionDiethyl ether was added
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-22f2b586f4df460ebfc8b35cdf5f2563
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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