Hydrochloric Acid → benzyl 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxylate

HRID 2271369Notes

Reaction equation

HRID 2271369 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH2:27][O:28][CH2:29][CH3:30])[C:23]([CH:31]([CH3:33])[CH3:32])=[CH:22][C:21]=1[C:34]1[N:38]([C:39]2[CH:40]=[C:41]3[C:45](=[CH:46][CH:47]=2)[N:44]([CH3:48])[CH:43]=[CH:42]3)[C:37](=[O:49])[NH:36][N:35]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C.Cl>ClCCl.CO>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH2:27][O:28][CH2:29][CH3:30])[C:23]([CH:31]([CH3:32])[CH3:33])=[CH:22][C:21]=1[C:34]1[N:38]([C:39]2[CH:40]=[C:41]3[C:45](=[CH:46][CH:47]=2)[N:44]([CH3:48])[CH:43]=[CH:42]3)[C:37](=[O:49])[N:36]([C:9]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[O:10])[N:35]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 67341299HCID 67341299, compound

Product 1

HCID 67339760benzyl 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Cbz-Cl was added to the solution of 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-1H-1,2,4-triazol-5(4H)-one and DIPEA in dichloromethane and reaction solution was stirred for 2 h at room temperature. Washed with water and extracted with dichloromethane and solvent was removed. The crude reaction mixture was carried over to the next reaction without further purification. The reaction mixture was diluted by methanol and treated with concentrated HCl and heated it up to 65° C. Column chromatogram produced the desired benzyl 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxylate.

Workup

  1. washWashed with water
  2. extractionextracted with dichloromethane and solvent
  3. customwas removed
  4. customThe crude reaction mixture
  5. customwas carried over to the next reaction without further purification
  6. temperatureheated it up to 65° C

Sources & evidence

ORD record
ord-3b8f9ee181bd412aaeb0eee78b901aca
Source dataset
uspto-grants-2015_09
Patent number
US09120745B2

Reaction notes

Loading…