3-[(1S,2S)-2-Hydroxycyclohexyl]-6-[(6-methyl-3-pyridinyl)methyl]benzo[h]quinazolin-4(3H)-one

Base Information

• Chemical Name: 3-[(1S,2S)-2-Hydroxycyclohexyl]-6-[(6-methyl-3-pyridinyl)methyl]benzo[h]quinazolin-4(3H)-one
• CAS No.: 1227923-29-6
• Molecular Formula: C25H25N3O2
• Molecular Weight: 399.492
• Mol file: 1227923-29-6.mol

Synonyms:3-[(1S,2S)-2-Hydroxycyclohexyl]-6-[(6-methyl-3-pyridinyl)methyl]benzo[h]quinazolin-4(3H)-one;M1 receptor;MK 7622;MK7622;MK-7622;3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-Methylpyridin-3-yl)Methyl)benzo[h]quinazolin-4(3H)-one

Chemical Property of 3-[(1S,2S)-2-Hydroxycyclohexyl]-6-[(6-methyl-3-pyridinyl)methyl]benzo[h]quinazolin-4(3H)-one

Chemical Property:

• PSA: 68.01000
• Density: 1.30
• LogP: 4.31990

Purity/Quality:

97% ^*data from raw suppliers

M1receptormodulator 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-[(1S,2S)-2-Hydroxycyclohexyl]-6-[(6-methyl-3-pyridinyl)methyl]benzo[h]quinazolin-4(3H)-one

There total 15 articles about 3-[(1S,2S)-2-Hydroxycyclohexyl]-6-[(6-methyl-3-pyridinyl)methyl]benzo[h]quinazolin-4(3H)-one 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: 95.0%

6-((6-chloropyridin-3-yl)methyl)-3-((1S,2S)-2-hydroxycyclohexyl)benzo[h]quinazolin-4(3H)-one (1227923-94-5) + methylzinc chloride (5158-46-3) → 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one (1227923-29-6)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; at 90 ℃; for 4.5h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.8b00095

Reference yield: 92.0%

5-acetoxymethyl-2-methyl-pyridine (34101-77-4) + 3-((1S,2S)-2-hydroxycyclohexyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[h]quinazolin-4(3H)-one (1227924-49-3) → 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one (1227923-29-6)

Guidance literature:

With palladium diacetate; potassium carbonate; ruphos; In water; isopropyl alcohol; at 82 ℃; for 1h;

Reference yield:

(1S,2S)-trans-2-aminocyclohexanol (931-15-7,931-16-8,6850-38-0,6982-39-4,33092-82-9,38898-70-3,74111-21-0,108267-20-5) → 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one (1227923-29-6)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / 15 h / 20 °C / Inert atmosphere

2: 2 h / 80 °C / Inert atmosphere

3: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 0.25 h / 0 - 20 °C / Inert atmosphere

4: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 4.5 h / 90 °C / Inert atmosphere

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran;

DOI:10.1021/acsmedchemlett.8b00095

upstream raw materials:

6-((6-chloropyridin-3-yl)methyl)-3-((1S,2S)-2-hydroxycyclohexyl)benzo[h]quinazolin-4(3H)-one

methylzinc chloride

1-amino-2-naphthoic acid

1-amino-4-bromo-2-naphthoic acid

Downstream raw materials:

3-((1S,2S)-2-((tert-butyldimethylsilyl)oxy)cyclohexyl)-6-((6-methylpyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

3-((1S,2S)-2-((tert-butyldimethylsilyl)oxy)cyclohexyl)-6-((6-methylpyridin-3-yl)methyl)-2,3-dihydrobenzo[h]quinazolin-4(1H)-one