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Cas Database

216979-24-7

216979-24-7

Identification

  • Product Name:3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

  • CAS Number: 216979-24-7

  • EINECS:

  • Molecular Weight:535.6

  • Molecular Formula: C28H33N5O6

  • HS Code:

  • Mol File:216979-24-7.mol

Synonyms:3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

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Relevant articles and documentsAll total 1 Articles be found

Efficacious, orally bioavailable thrombin inhibitors based on 3- aminopyridinone or 3-aminopyrazinone acetamide peptidomimetic templates

Sanderson, Philip E. J.,Lyle, Terry A.,Cutrona, Kellie J.,Dyer, Dona L.,Dorsey, Bruce D.,McDonough, Colleen M.,Naylor-Olsen, Adel M.,Chen, I.-Wu,Chen, Zhongguo,Cook, Jacquelynn J.,Cooper, Carolyn M.,Gardell, Stephen J.,Hare, Timothy R.,Krueger, Julie A.,Lewis, S. Dale,Lin, Jiunn H.,Lucas Jr., Bobby J.,Lyle, Elizabeth A.,Lynch Jr., Joseph J.,Stranieri, Maria T.,Vastag, Kari,Yan, Youwei,Shafer, Jules A.,Vacca, Joseph P.

, p. 4466 - 4474 (2007/10/03)

We have addressed the key deficiency of noncovalent pyridinone acetamide thrombin inhibitor L-374,087 (1), namely, its modest half-lives in animals, by making a chemically stable 3-alkylaminopyrazinone bioisostere for its 3- sulfonylaminopyridinone core.

Process route upstream and downstream products

Process route

(3-Benzyloxycarbonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetic acid
147269-63-4

(3-Benzyloxycarbonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetic acid

2-tert-butoxycarbonylamino-5-aminomethyl-6-methyl-pyridine
187163-72-0

2-tert-butoxycarbonylamino-5-aminomethyl-6-methyl-pyridine

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; for 64h;
84%
5-bromo-6-methyl-pyridin-2-ylamine
42753-71-9

5-bromo-6-methyl-pyridin-2-ylamine

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 85 percent / dimethylformamide / 4 h / Heating
2: 84 percent / Et3N, DMAP / CH2Cl2
3: 69 percent / H2 / Pd/C / acetic acid / 60 h / 3102.89 Torr
4: 84 percent / EDC hydrochloride, HOBT, Et3N / dimethylformamide / 64 h
With dmap; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In dichloromethane; acetic acid; N,N-dimethyl-formamide;
2-amino-5-cyano-6-methylpyridine
183428-90-2

2-amino-5-cyano-6-methylpyridine

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 84 percent / Et3N, DMAP / CH2Cl2
2: 69 percent / H2 / Pd/C / acetic acid / 60 h / 3102.89 Torr
3: 84 percent / EDC hydrochloride, HOBT, Et3N / dimethylformamide / 64 h
With dmap; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In dichloromethane; acetic acid; N,N-dimethyl-formamide;
2-tert-butoxycarbonylamino-5-cyano-6-methylpyridine
187163-71-9

2-tert-butoxycarbonylamino-5-cyano-6-methylpyridine

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 69 percent / H2 / Pd/C / acetic acid / 60 h / 3102.89 Torr
2: 84 percent / EDC hydrochloride, HOBT, Et3N / dimethylformamide / 64 h
With hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In acetic acid; N,N-dimethyl-formamide;
2-hydroxy-6-methylnicotinic acid
38116-61-9

2-hydroxy-6-methylnicotinic acid

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1.)DPPA, Et3N / 1.) dioxane, reflux, 16 h, 2.) dioxane, reflux, 24 h
2: 97 percent / NaH / 1.) from 0 deg C to RT, 2.) RT, 2 h
3: HCl(gas) / ethyl acetate / 1 h / Ambient temperature
4: 84 percent / EDC hydrochloride, HOBT, Et3N / dimethylformamide / 64 h
With hydrogenchloride; diphenyl-phosphinic acid; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;
benzyl N-(6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)carbamate
147269-61-2

benzyl N-(6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)carbamate

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 97 percent / NaH / 1.) from 0 deg C to RT, 2.) RT, 2 h
2: HCl(gas) / ethyl acetate / 1 h / Ambient temperature
3: 84 percent / EDC hydrochloride, HOBT, Et3N / dimethylformamide / 64 h
With hydrogenchloride; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;
2-[6-methyl-2-oxo-3-(benzyloxycarbonylamino)-2H-pyridin-1-yl]acetic acid t-butyl ester
179524-33-5

2-[6-methyl-2-oxo-3-(benzyloxycarbonylamino)-2H-pyridin-1-yl]acetic acid t-butyl ester

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: HCl(gas) / ethyl acetate / 1 h / Ambient temperature
2: 84 percent / EDC hydrochloride, HOBT, Et3N / dimethylformamide / 64 h
With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;
benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1.)DPPA, Et3N / 1.) dioxane, reflux, 16 h, 2.) dioxane, reflux, 24 h
2: 97 percent / NaH / 1.) from 0 deg C to RT, 2.) RT, 2 h
3: HCl(gas) / ethyl acetate / 1 h / Ambient temperature
4: 84 percent / EDC hydrochloride, HOBT, Et3N / dimethylformamide / 64 h
With hydrogenchloride; diphenyl-phosphinic acid; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;
3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

3-(2-phenethylamino)-6-methyl-1-(2-amino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

3-(2-phenethylamino)-6-methyl-1-(2-amino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: H2 / Pearlman's catalyst / ethanol; H2O / 2 h / 3102.89 Torr
2: NaBH(OAc)3, acetic acid / 1,2-dichloro-ethane / 16 h
3: HCl(gas) / ethyl acetate / 0.25 h / 0 °C
With hydrogenchloride; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; palladium dihydroxide; In ethanol; water; ethyl acetate; 1,2-dichloro-ethane;
3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone
216979-24-7

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

3-(2-phenethylamino)-6-methyl-1-(2-tert-butylcarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

3-(2-phenethylamino)-6-methyl-1-(2-tert-butylcarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: H2 / Pearlman's catalyst / ethanol; H2O / 2 h / 3102.89 Torr
2: NaBH(OAc)3, acetic acid / 1,2-dichloro-ethane / 16 h
With hydrogen; sodium tris(acetoxy)borohydride; acetic acid; palladium dihydroxide; In ethanol; water; 1,2-dichloro-ethane;

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