tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate
CAS No.:912368-71-9
Molecular Formula:C₂₄H₂₆N₄O₂S
Molecular Weight:434.562
Hs Code.:

Synonyms:tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate

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Chemical Property of tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate

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Technology Process of tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate

There total 8 articles about tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate 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: 78.0%

: 912368-70-8
tert-butyl (3S)-3-[(7-cyano-2-bromothieno[3,2-c]pyridin-4-yl)amino]piperidine-1-carboxylate

: 98-80-6
phenylboronic acid

: 912368-71-9
tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 80 ℃; for 1h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.7b01490

Reference yield:

: 20893-30-5
2-cyanomethylthiophene

: 912368-71-9
tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium carbonate / methanol / 2 h / Inert atmosphere; Reflux

2.1: oxalyl dichloride / dichloromethane / 1 h / 20 °C

3.1: sodium azide / 1,4-dioxane; water / 0 - 20 °C

4.1: tributyl-amine / dichloromethane; diphenylether / 2.17 h / 210 °C / Inert atmosphere

5.1: N-Bromosuccinimide; acetic acid / N,N-dimethyl-formamide / 12 h / 80 °C

5.2: 20 °C / pH 9 - 10

6.1: trichlorophosphate / Reflux

7.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 80 °C

8.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / 80 °C / Inert atmosphere

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; oxalyl dichloride; tributyl-amine; potassium carbonate; caesium carbonate; acetic acid; trichlorophosphate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; diphenylether; dichloromethane; water; N,N-dimethyl-formamide; 1.1: |Knoevenagel Condensation / 4.1: |Curtius Rearrangement / 8.1: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.7b01490

Reference yield:

: 912368-68-4
(2Z)-3-cyano-3-(2-thienyl)acryloyl chloride

: 912368-71-9
tert-butyl (3S)-3-{[7-cyano-2-(phenyl)thieno[3,2-c]pyridin-4-yl]amino}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium azide / 1,4-dioxane; water / 0 - 20 °C

2.1: tributyl-amine / dichloromethane; diphenylether / 2.17 h / 210 °C / Inert atmosphere

3.1: N-Bromosuccinimide; acetic acid / N,N-dimethyl-formamide / 12 h / 80 °C

3.2: 20 °C / pH 9 - 10

4.1: trichlorophosphate / Reflux

5.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 80 °C

6.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / 80 °C / Inert atmosphere

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; tributyl-amine; potassium carbonate; caesium carbonate; acetic acid; trichlorophosphate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; diphenylether; dichloromethane; water; N,N-dimethyl-formamide; 2.1: |Curtius Rearrangement / 6.1: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.7b01490