3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene

Base Information

• Chemical Name: 3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene
• CAS No.: 174298-73-8
• Molecular Formula: C₃₈H₄₄N₄O₄Si
• Molecular Weight: 648.877
• Mol file: 174298-73-8.mol

Synonyms:

Chemical Property of 3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene

There total 11 articles about 3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene 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:

2,6-dimethylbenzyl alcohol (62285-58-9) → 3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene (174298-73-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 98.2 percent / DMAP / 5 h / 70 °C

2: 94.3 percent / Cu(NO₃)2*3H₂O, Ac₂O, AcOH / 1 h / 0 - 20 °C

3: 1 N NaOH / methanol

4: imidazole / dimethylformamide / 3 h / Ambient temperature

5: FeCl₃*6H₂O, C, NH₂-NH₂*H₂O / methanol; H₂O / 5 h / 70 °C

6: Et₃N / CH₂Cl₂ / 1.5 h / 0 - 20 °C

7: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 2 h

8: NH₂-NH₂*H₂O / ethanol / 1 h / Heating

9: WSCD*HCl, HOBt / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; dmap; sodium hydroxide; WSCD*HCl; acetic anhydride; iron(III) chloride; sodium hydride; benzotriazol-1-ol; copper(II) nitrate; hydrazine hydrate; acetic acid; triethylamine; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm980300f

Reference yield:

2,6-dimethylbenzyl acetate (62346-87-6) → 3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene (174298-73-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 94.3 percent / Cu(NO₃)2*3H₂O, Ac₂O, AcOH / 1 h / 0 - 20 °C

2: 1 N NaOH / methanol

3: imidazole / dimethylformamide / 3 h / Ambient temperature

4: FeCl₃*6H₂O, C, NH₂-NH₂*H₂O / methanol; H₂O / 5 h / 70 °C

5: Et₃N / CH₂Cl₂ / 1.5 h / 0 - 20 °C

6: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 2 h

7: NH₂-NH₂*H₂O / ethanol / 1 h / Heating

8: WSCD*HCl, HOBt / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; WSCD*HCl; acetic anhydride; iron(III) chloride; sodium hydride; benzotriazol-1-ol; copper(II) nitrate; hydrazine hydrate; acetic acid; triethylamine; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm980300f

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3-[N-[(E)-3-(6-Acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene (174298-73-8)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 3 h / Ambient temperature

2: FeCl₃*6H₂O, C, NH₂-NH₂*H₂O / methanol; H₂O / 5 h / 70 °C

3: Et₃N / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 2 h

5: NH₂-NH₂*H₂O / ethanol / 1 h / Heating

6: WSCD*HCl, HOBt / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; WSCD*HCl; iron(III) chloride; sodium hydride; benzotriazol-1-ol; hydrazine hydrate; triethylamine; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm980300f

upstream raw materials:

3-(N-Glycyl-N-methylamino)-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene

(E)-3-(6-acetylamino-pyridin-3-yl)acrylic acid

2,6-dimethylbenzyl alcohol

2,6-dimethylbenzyl acetate

Downstream raw materials:

3-[N-[(E)-3-(6-acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dimethylbenzyl chloride

3-[N-[(E)-3-(6-acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-hydroxymethyl-2,6-dimethylbenzene

Refernces

• 1、 Abe, Yoshito,Kayakiri, Hiroshi,Satoh, Shigeki,Inoue, Takayuki,Sawada, Yuki,Inamura, Noriaki,Asano, Masayuki,Aramori, Ichiro,Hatori, Chie,Sawai, Hiroe,Oku, Teruo,Tanaka, Hirokazu. "A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 3. Discovering bioisosteres of the imidazo[1,2-a]pyridine moiety". . p. 4062 - 4079. Retrieved 2007/10/03.