Technology Process of (3S)-3-(2-aminocinnamoyl)amino-1-(2-fluorophenyl)-3,4,6,7-tetrahydropyrrolo<3,2,1-jk><1,4>benzodiazepin-4(3H)-one
There total 11 articles about (3S)-3-(2-aminocinnamoyl)amino-1-(2-fluorophenyl)-3,4,6,7-tetrahydropyrrolo<3,2,1-jk><1,4>benzodiazepin-4(3H)-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
N,N-dimethyl-formamide;
at 0 - 20 ℃;
for 0.5h;
DOI:10.1248/cpb.42.2071
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 1.) BCl3, AlCl3, 2.) 2N aq. HCl / 1.) toluene, reflux, 16 h, 2.) toluene, reflux, 2.5 h
2: 96 percent / pyridine / CH2Cl2 / 1 h / 0 °C
3: 90.3 percent / 50percent aq. NaOH, NH2OH*HCl / ethanol / 2.5 h / 50 - 55 °C
4: 91.8 percent / 10 h / 105 °C
5: 95.8 percent / 1 N aq. NaOH / ethanol / 0.5 h
6: (iso-Pr)2NEt / CH2Cl2 / 1 h / Ambient temperature
7: methanol. NH3 / CH2Cl2 / 2 h / Ambient temperature
8: via diastereomeric salt formation with L-(+)-tartaric acid with a catalytic amount of 3,5-dichlorosalicylaldehyde
9: 1-hydroxybenzotriazole, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, Et3N / dimethylformamide / 0.5 h / 0 - 20 °C
With
pyridine; hydrogenchloride; sodium hydroxide; aluminium trichloride; hydroxylamine hydrochloride; ammonia; boron trichloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine;
In
ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.42.2071
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 1.) BCl3, AlCl3, 2.) 2N aq. HCl / 1.) toluene, reflux, 16 h, 2.) toluene, reflux, 2.5 h
2: 96 percent / pyridine / CH2Cl2 / 1 h / 0 °C
3: 90.3 percent / 50percent aq. NaOH, NH2OH*HCl / ethanol / 2.5 h / 50 - 55 °C
4: 91.8 percent / 10 h / 105 °C
5: 95.8 percent / 1 N aq. NaOH / ethanol / 0.5 h
6: (iso-Pr)2NEt / CH2Cl2 / 1 h / Ambient temperature
7: methanol. NH3 / CH2Cl2 / 2 h / Ambient temperature
8: via diastereomeric salt formation with L-(+)-tartaric acid with a catalytic amount of 3,5-dichlorosalicylaldehyde
9: 1-hydroxybenzotriazole, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, Et3N / dimethylformamide / 0.5 h / 0 - 20 °C
With
pyridine; hydrogenchloride; sodium hydroxide; aluminium trichloride; hydroxylamine hydrochloride; ammonia; boron trichloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine;
In
ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.42.2071