4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile

Base Information

Chemical Name:4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile
CAS No.:912369-04-1
Molecular Formula:C₂₀H₂₀N₄S
Molecular Weight:348.472
Hs Code.:

Synonyms:4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile

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Chemical Property of 4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile

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Technology Process of 4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile

There total 10 articles about 4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile 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:

: 625471-18-3
tert-butyl (3S)-3-aminopiperidine-1-carboxylate

: 912369-04-1
4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: potassium carbonate / 1-methyl-pyrrolidin-2-one / 130 °C

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

With lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; water; 3: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.7b01490

Reference yield:

: 2-bromo-4-{[(3S)-1-methylpiperidin-3-yl]amino}thieno[3,2-c]pyridine-7-carbonitrile

: 98-80-6
phenylboronic acid

: 912369-04-1
4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile

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

: 912369-04-1
4-{[(3S)-1-methylpiperidin-3-yl]amino}-2-phenylthieno[3,2-c]pyridine-7-carbonitrile

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 / 130 °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