N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide

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Chemical Name:N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide
CAS No.:1350968-83-0
Molecular Formula:C₂₇H₃₅N₅O₃
Molecular Weight:477.607
Hs Code.:

Synonyms:N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide

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Chemical Property of N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide

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Technology Process of N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide

There total 11 articles about N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide 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:

: 1-(1-methyl-1H-pyrazol-4-yl)piperazine hydrochloride

: 1350968-96-5
4-formyl-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-2-naphthamide

: 1350968-83-0
N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide

Guidance literature:: With sodium tris(acetoxy)borohydride; acetic acid; triethylamine; In 1,2-dichloro-ethane; for 18h;

Reference yield:

: 5813-38-7
methyl 1-methoxy-4-bromo-2-naphthoate

: 1350968-83-0
N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; water / 80 °C

2: sodium hydroxide / tetrahydrofuran; water

3: triethylamine / dichloromethane

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone

5: sodium tris(acetoxy)borohydride / dichloromethane

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; osmium(VIII) oxide; sodium tris(acetoxy)borohydride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; acetone; 1: |Suzuki Coupling;
DOI:10.1016/j.bmcl.2014.01.012

Reference yield:

: 86-48-6
1-hydroxy-2-naphthoic acid

: 1350968-83-0
N[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-4-{[4-(1-methyl-1H-pyrazol-4-yl)piperazin-1-yl]methyl}-2-naphthamide

Guidance literature:: Multi-step reaction with 7 steps

1: bromine / acetic acid / 72 h

2: potassium carbonate / acetone / 14 h / 20 °C / Reflux

3: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 65 h / 65 °C / Inert atmosphere

4: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water; acetone / 2 h

5: water; sodium hydroxide / tetrahydrofuran / 65 h / 50 °C

6: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 24 h

7: sodium tris(acetoxy)borohydride; acetic acid; triethylamine / 1,2-dichloro-ethane / 18 h

With sodium periodate; osmium(VIII) oxide; water; bromine; sodium tris(acetoxy)borohydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;