4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile

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Chemical Name:4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile
CAS No.:1259522-91-2
Molecular Formula:C₂₆H₂₂FN₇O₂
Molecular Weight:483.505
Hs Code.:

Synonyms:4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile

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Chemical Property of 4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile

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Technology Process of 4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile

There total 11 articles about 4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile 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: 71.0%

: 45347-82-8
azetidine-3-ol

: 1259523-28-8
(S)-2-(1-(6-amino-5-cyanopyrimidin-4-ylamino)ethyl)-6-fluoro-3-phenylquinoline-4-carboxylic acid

: 1259522-91-2
4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/acs.jmedchem.6b00827

Reference yield:

: 2-ethyl-6-fluoro-3-phenylquinoline-4-carboxylic acid

: 1259522-91-2
4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1.1: thionyl chloride / dichloromethane / 20 °C

1.2: 2 h / 20 °C

2.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; dibenzoyl peroxide / tetrachloromethane / 3 h / Reflux

3.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 3 h / 120 °C

6.1: lithium iodide / pyridine / 100 °C

7.1: AD-H column / isopropyl alcohol; diethylamine / Resolution of racemate

8.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

With thionyl chloride; sodium azide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; palladium 10% on activated carbon; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; lithium iodide; dibenzoyl peroxide; In pyridine; methanol; tetrachloromethane; dichloromethane; diethylamine; N,N-dimethyl-formamide; isopropyl alcohol; butan-1-ol;
DOI:10.1021/acs.jmedchem.6b00827

Reference yield:

: 1259522-28-5
methyl 2-(1-aminoethyl)-6-fluoro-3-phenylquinoline-4-carboxylate

: 1259522-91-2
4-amino-6-(((1S)-1-(6-fluoro-4-((3-hydroxy-1-azetidinyl)-carbonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 3 h / 120 °C

2: lithium iodide / pyridine / 100 °C

3: AD-H column / isopropyl alcohol; diethylamine / Resolution of racemate

4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium iodide; In pyridine; diethylamine; N,N-dimethyl-formamide; isopropyl alcohol; butan-1-ol;
DOI:10.1021/acs.jmedchem.6b00827