rac trans-Lafutidine

Base Information

• Chemical Name: rac trans-Lafutidine
• CAS No.: 206449-94-7
• Molecular Formula: C22H29N3O4S
• Molecular Weight: 431.55
• European Community (EC) Number: 601-513-8
• DSSTox Substance ID: DTXSID301110782
• Nikkaji Number: J956.752F
• Wikipedia: Lafutidine
• Mol file: 206449-94-7.mol

Synonyms:rac trans-Lafutidine;206449-94-7;2-(furan-2-ylmethylsulfinyl)-N-[(E)-4-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxybut-2-enyl]acetamide;rac Lafutidine;118288-08-7;SCHEMBL3855528;DTXSID301110782;2-((Furan-2-ylMethyl)sulfinyl)-N-(4-((4-(piperidin-1-ylMethyl)pyridin-2-yl)oxy)but-2-en-1-yl)acetaMide;2-[(RS)-Furan-2-ylmethylsulfinyl]-N-{4-[4-(piperidin-1-ylmethyl) pyridin-2-yl]oxy-(2Z)-but-2-en-1-yl}acetamide;2-[(2-Furanylmethyl)sulfinyl]-N-[(2E)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-yl]acetamide;J-013489;(E)-2-(furan-2-ylmethylsulfinyl)-N-(4-(4-(piperidin-1-ylmethyl)pyridin-2-yloxy)but-2-enyl)acetamide;2-[(furan-2-yl)methanesulfinyl]-N-[(2E)-4-({4-[(piperidin-1-yl)methyl]pyridin-2-yl}oxy)but-2-en-1-yl]acetamide;2-[[(2-Furyl)methyl]sulfinyl]-N-[(E)-4-[[4-(piperidinomethyl)-2-pyridyl]oxy]-2-butenyl]acetamide

Chemical Property of rac trans-Lafutidine

Chemical Property:

• PSA: 107.37000
• LogP: 4.30450
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 431.18787759
• Heavy Atom Count: 30
• Complexity: 569

Purity/Quality:

99% ^*data from raw suppliers

ractrans-Lafutidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)CC2=CC(=NC=C2)OCC=CCNC(=O)CS(=O)CC3=CC=CO3
• Isomeric SMILES: C1CCN(CC1)CC2=CC(=NC=C2)OC/C=C/CNC(=O)CS(=O)CC3=CC=CO3
• Uses: A trans isomeric impurity of rac Lafutidine (L168500).

Technology Process of rac trans-Lafutidine

There total 13 articles about rac trans-Lafutidine 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: 94.6%

(2Z)-4-({4-[(piperidin-1-yl)methyl]pyridin-2-yl}oxy)but-2-en-1-amine + p-nitrophenyl 2-(furfurylsulfinyl)acetate (123855-55-0) → lafutidine (118288-08-7,206449-93-6,206449-94-7)

Guidance literature:

In dichloromethane; at 25 - 30 ℃;

Reference yield:

2-Bromo-4-[1,3]dioxolan-2-yl-pyridine (118289-18-2) → lafutidine (118288-08-7,206449-93-6,206449-94-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / NaOH, K₂CO₃, n-Bu₄NHSO₄ / toluene / 18 h / Ambient temperature

2: 90 percent / pyridinium p-toluenesulfonate, ethanol / 18 h / 55 °C

3: SOCl₂, Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: n-Bu₄NHSO₄ / acetonitrile / 18 h / Heating

5: 78 percent / NH₂NH₂*H₂O / methanol / 10 h / Heating

6: 91 percent / tetrahydrofuran / 18 h / Ambient temperature

7: 52 percent / p-TsOH, H₂O / acetone / 18 h / Heating

8: 2.) NaBH₄ / 1.) EtOH, 3 h, 2.) EtOH, 16 h

With sodium hydroxide; sodium tetrahydroborate; thionyl chloride; ethanol; water; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; acetonitrile;

DOI:10.1248/cpb.46.616

Reference yield:

(Z)-4-(4-[1,3]Dioxolan-2-yl-pyridin-2-yloxy)-but-2-enylamine (118289-22-8) → lafutidine (118288-08-7,206449-93-6,206449-94-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / tetrahydrofuran / 18 h / Ambient temperature

2: 52 percent / p-TsOH, H₂O / acetone / 18 h / Heating

3: 2.) NaBH₄ / 1.) EtOH, 3 h, 2.) EtOH, 16 h

With sodium tetrahydroborate; water; toluene-4-sulfonic acid; In tetrahydrofuran; acetone;

DOI:10.1248/cpb.46.616

upstream raw materials:

piperidine

N-[(Z)-4-(4-Formyl-pyridin-2-yloxy)-but-2-enyl]-2-(furan-2-ylmethanesulfinyl)-acetamide

2-Bromo-4-[1,3]dioxolan-2-yl-pyridine

(Z)-4-(4-[1,3]Dioxolan-2-yl-pyridin-2-yloxy)-but-2-enylamine

Refernces

• 1、 -. "Preparation method and application of lafutidine and intermediate thereof". Paragraph 0107-0108; 0111-0115; 0118-0122; 0125-0129; 0132. . Retrieved 2020/01/12.
• 2、 -. "Lafutidine hydroxylamine hydrochloride method of preparation". Paragraph 0043-0044. . Retrieved 2016/10/08.