Technology Process of 3-chloro-N-{(1S)-2-[(N-methylglycyl)amino]-1-[(4-{8-[(1S)-1-hydroxyethyl]imidazo[1,2-a]pyridin-2-yl}phenyl)methyl]ethyl}-4-[(1-methylethyl)oxy]benzamide
There total 21 articles about 3-chloro-N-{(1S)-2-[(N-methylglycyl)amino]-1-[(4-{8-[(1S)-1-hydroxyethyl]imidazo[1,2-a]pyridin-2-yl}phenyl)methyl]ethyl}-4-[(1-methylethyl)oxy]benzamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 5 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction
2.2: 0 °C / Large scale reaction
3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C
3.2: 40 °C
4.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C
5.1: tetrahydrofuran; methanol / 23 h / -5 °C / Inert atmosphere
With
dipotassium hydrogenphosphate; oxalyl dichloride; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide;
In
tetrahydrofuran; 2-methyltetrahydrofuran; methanol; ethanol; dichloromethane; tert-butyl methyl ether; water; toluene;
4.1: Schotten-Baumann reaction;
DOI:10.1021/op100186c
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C
1.2: 50 °C
2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C
2.2: 50 - 60 °C
3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C
4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction
5.2: 0 °C / Large scale reaction
6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C
6.2: 40 °C
7.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C
8.1: tetrahydrofuran; methanol / 23 h / -5 °C / Inert atmosphere
With
dipotassium hydrogenphosphate; N-chloro-succinimide; oxalyl dichloride; water; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; potassium hydroxide;
In
tetrahydrofuran; 2-methyltetrahydrofuran; methanol; ethanol; dichloromethane; tert-butyl methyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
7.1: Schotten-Baumann reaction;
DOI:10.1021/op100186c
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C
1.2: 2 h / 60 °C
2.1: aluminum (III) chloride / 22 h / -5 °C
2.2: 35 - 50 °C
2.3: 18 h / 65 °C
3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C
4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction
5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C
5.2: 40 °C
6.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C
7.1: tetrahydrofuran; methanol / 23 h / -5 °C / Inert atmosphere
With
aluminum (III) chloride; dipotassium hydrogenphosphate; di-isopropyl azodicarboxylate; tetrabutylammomium bromide; sodium hydrogencarbonate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; 2-methyltetrahydrofuran; methanol; ethanol; tert-butyl methyl ether; water; toluene; acetonitrile;
1.1: Mitsunobu reaction / 2.1: Friedel Crafts acylation / 6.1: Schotten-Baumann reaction;
DOI:10.1021/op100186c
