N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide

Base Information

Chemical Name:N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide
CAS No.:1376918-87-4
Molecular Formula:C₂₀H₂₀N₄O₂S
Molecular Weight:380.47
Hs Code.:

Synonyms:N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide

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Chemical Property of N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide

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Technology Process of N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide

There total 11 articles about N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

: 1376918-50-1
6-amino-3-benzylamino-9H-β-carboline

: 594-44-5
Ethanesulfonyl chloride

: 1376918-87-4
N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere; Reflux;
DOI:10.1016/j.bmcl.2012.03.077

Reference yield:

: 79815-18-2
methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

: 1376918-87-4
N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide

Guidance literature:: Multi-step reaction with 11 steps

1: trichloroisocyanuric acid; triethylamine / N,N-dimethyl-formamide / 2 h / -20 - 0 °C / Inert atmosphere

2: hydrazine hydrate / pentan-1-ol / 7 h / Reflux; Inert atmosphere

3: hydrogenchloride; sodium nitrite / water / 2 h / 0 °C / Inert atmosphere

4: acetic acid / water / 1 h / Reflux

5: chloroform / 1 h / Reflux; Inert atmosphere

6: sodium nitrate; trifluoroacetic acid / 18 h / 0 - 20 °C / Inert atmosphere

7: hydrogenchloride / water / 12 h / Reflux; Inert atmosphere

8: acetic acid / methanol / 4 h / 20 °C / pH 4 / Inert atmosphere

9: sodium cyanoborohydride / methanol / 1 h / 20 °C / Inert atmosphere

10: hydrogenchloride; tin(II) chloride dihdyrate / methanol; water / 48 h / 0 - 20 °C / Inert atmosphere

11: dmap; triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere; Reflux

With hydrogenchloride; dmap; sodium nitrate; tin(II) chloride dihdyrate; trichloroisocyanuric acid; sodium cyanoborohydride; hydrazine hydrate; acetic acid; triethylamine; trifluoroacetic acid; sodium nitrite; In methanol; dichloromethane; pentan-1-ol; chloroform; water; N,N-dimethyl-formamide; 4: Curtius rearrangement;
DOI:10.1016/j.bmcl.2012.03.077

Reference yield:

: 73-22-3,27732-43-0,80206-30-0,27813-82-7
L-Tryptophan

: 1376918-87-4
N-(3-(benzylamino)-9H-β-carbolin-6-yl)ethanesulfonamide

Guidance literature:: Multi-step reaction with 13 steps

1: sodium hydroxide / water / 5 h / 20 °C / Reflux; Inert atmosphere

2: thionyl chloride / 24 h / 0 °C / Reflux; Inert atmosphere

3: trichloroisocyanuric acid; triethylamine / N,N-dimethyl-formamide / 2 h / -20 - 0 °C / Inert atmosphere

4: hydrazine hydrate / pentan-1-ol / 7 h / Reflux; Inert atmosphere

5: hydrogenchloride; sodium nitrite / water / 2 h / 0 °C / Inert atmosphere

6: acetic acid / water / 1 h / Reflux

7: chloroform / 1 h / Reflux; Inert atmosphere

8: sodium nitrate; trifluoroacetic acid / 18 h / 0 - 20 °C / Inert atmosphere

9: hydrogenchloride / water / 12 h / Reflux; Inert atmosphere

10: acetic acid / methanol / 4 h / 20 °C / pH 4 / Inert atmosphere

11: sodium cyanoborohydride / methanol / 1 h / 20 °C / Inert atmosphere

12: hydrogenchloride; tin(II) chloride dihdyrate / methanol; water / 48 h / 0 - 20 °C / Inert atmosphere

13: dmap; triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere; Reflux

With hydrogenchloride; dmap; sodium nitrate; thionyl chloride; tin(II) chloride dihdyrate; trichloroisocyanuric acid; sodium cyanoborohydride; hydrazine hydrate; acetic acid; triethylamine; trifluoroacetic acid; sodium hydroxide; sodium nitrite; In methanol; dichloromethane; pentan-1-ol; chloroform; water; N,N-dimethyl-formamide; 1: Pictet-Spengler cyclisation / 6: Curtius rearrangement;
DOI:10.1016/j.bmcl.2012.03.077