Triethylamine → HCID 19085257, compound

HRID 963063Notes

Reaction equation

HRID 963063 reaction equation
N[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C=C[CH:7]=1.C([N:18]([CH2:21]C)[CH2:19][CH3:20])C.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:45][CH2:46][C:47]1[N:51]([C:52]2[S:53][C:54]([CH2:66][CH3:67])=[CH:55][C:56]=2[C:57](=[O:65])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[Cl:64])[C:50]([CH3:68])=[N:49][N:48]=1>O1CCCC1>[Cl:64][C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=1[C:57]([C:56]1[CH:55]=[C:54]([CH2:66][CH3:67])[S:53][C:52]=1[N:51]1[C:50]([CH3:68])=[N:49][N:48]=[C:47]1[CH2:46][NH:45][C:21](=[O:30])[NH:18][C:19]1[CH:20]=[C:4]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]=[CH:2][CH:7]=1)=[O:65]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 190850953-Aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole ditosylateHCID 21201528tert-butyl 2-(3-aminophenyl)acetate

Product 1

HCID 19085257HCID 19085257, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-aminophenylacetate (2.07 g) was dissolved in tetrahydrofuran (70 ml), and N,N'-carbonyldiimidazole (1.7 g) was added under ice-cooling. One hour later, triethylamine (2.8 ml) and 3-aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole di-p-toluenesulfonate (7.42 g) were added, and the mixture was stirred at room temperature for one day. The reaction mixture was concentrated, and partitioned between ethyl acetate and water. The organic layer was washed with a 5% aqueous citric acid solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and crude crystals (2.58 g) were precipitated from a small amount of ethyl acetate. The crystals were recrystallized from ethyl acetate to give 1.66 g of tert-butyl 3-(3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)ureido)phenylacetate.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with a 5% aqueous citric acid solution
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customcrude crystals (2.58 g) were precipitated from a small amount of ethyl acetate
  8. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7e7652ffa5874448b8677af1df4a343e
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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