5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile

Base Information

Chemical Name:5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile
CAS No.:1426696-64-1
Molecular Formula:C₂₃H₂₇F₂N₇O
Molecular Weight:455.51
Hs Code.:

Synonyms:5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile

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Chemical Property of 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile

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Technology Process of 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile

There total 14 articles about 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile 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: 30.0%

: 557-21-1
zinc(II) cyanide

: 1426696-63-0
1-{1-[5-chloro-3-(1-isopropylazetidin-3-yl)-2-methoxy-4-methylphenyl]ethyl}-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

: 1426696-64-1
5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile

Guidance literature:: With sulfuric acid; palladium diacetate; zinc; XPhos; In N,N-dimethyl acetamide; at 120 ℃; Inert atmosphere;

Reference yield:

: 1382996-71-5
tert-butyl 3-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)azetidine-1-carboxylate

: 1426696-64-1
5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile

Guidance literature:: Multi-step reaction with 12 steps

1: sodium tetrahydroborate; methanol / 1 h / 0 - 5 °C

2: 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide / dichloromethane / 20 °C

3: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 120 °C

4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5: triethylamine / acetonitrile / 20 °C

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide; water / 3 h / 100 °C / Inert atmosphere

7: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / tert-butyl alcohol / 20 °C

8: sodium periodate; acetic acid / water; tetrahydrofuran / 3 h / 0 °C

9: diethylamino-sulfur trifluoride / dichloromethane / 2.5 h / 0 - 20 °C

10: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C

11: triethylamine / dichloromethane / 2 h / 20 °C

12: zinc; sulfuric acid; palladium diacetate; XPhos / N,N-dimethyl acetamide / 120 °C / Inert atmosphere

With hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3,5-trichloro-2,4,6-triazine; diethylamino-sulfur trifluoride; sulfuric acid; water; palladium diacetate; sodium carbonate; caesium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; potassium iodide; zinc; XPhos; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

: 1426699-08-2
tert-butyl 3-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]azetidine-1-carboxylate

: 1426696-64-1
5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-(1-isopropylazetidin-3-yl)-4-methoxy-2-methylbenzonitrile

Guidance literature:: Multi-step reaction with 10 steps

1: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 120 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

3: triethylamine / acetonitrile / 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide; water / 3 h / 100 °C / Inert atmosphere

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / tert-butyl alcohol / 20 °C

6: sodium periodate; acetic acid / water; tetrahydrofuran / 3 h / 0 °C

7: diethylamino-sulfur trifluoride / dichloromethane / 2.5 h / 0 - 20 °C

8: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C

9: triethylamine / dichloromethane / 2 h / 20 °C

10: zinc; sulfuric acid; palladium diacetate; XPhos / N,N-dimethyl acetamide / 120 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamino-sulfur trifluoride; sulfuric acid; water; palladium diacetate; sodium carbonate; caesium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; potassium iodide; zinc; XPhos; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;