N₁-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N₂,N₂-dimethylglycinamide

Base Information

• Chemical Name: N₁-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N₂,N₂-dimethylglycinamide
• CAS No.: 916051-31-5
• Molecular Formula: C₂₄H₂₂ClN₅O₂S
• Molecular Weight: 479.99

Synonyms:N₁-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N₂,N₂-dimethylglycinamide

Chemical Property of N₁-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N₂,N₂-dimethylglycinamide

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Technology Process of N₁-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N₂,N₂-dimethylglycinamide

There total 3 articles about N₁-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N₂,N₂-dimethylglycinamide 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: 55.0%

(5Z)-2-{[5-(aminomethyl)-2-chlorophenyl]amino}-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one (916050-72-1) + N,N-dimethylglycine hydrochoride (2491-06-7) → N1-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N2,N2-dimethylglycinamide (916051-31-5)

Guidance literature:

(5Z)-2-{[5-(aminomethyl)-2-chlorophenyl]amino}-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one; N,N-dimethylglycine hydrochoride; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 18h;

With sodium hydroxide; In water; N,N-dimethyl-formamide; pH=7;

Reference yield:

1,1-dimethylethyl ({4-chloro-3-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]phenyl}methyl)carbamate → N1-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N2,N2-dimethylglycinamide (916051-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: piperdinium acetate / ethanol; toluene / 18 h / Heating / reflux

2.1: trifluoroacetic acid / 0.33 h

2.3: pH 8

3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 18 h

3.2: pH 7

With 1-hydroxy-7-aza-benzotriazole; piperdinium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In ethanol; N,N-dimethyl-formamide; toluene;

Reference yield:

N-(3-amino-4-chlorophenylmethyl)carbamic acid t-butyl ester (180081-30-5) → N1-[(4-chloro-3-{[(5Z)-4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}phenyl)methyl]-N2,N2-dimethylglycinamide (916051-31-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethanol / 40 h / Heating / reflux

2.1: piperdinium acetate / ethanol; toluene / 18 h / Heating / reflux

3.1: trifluoroacetic acid / 0.33 h

3.3: pH 8

4.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 18 h

4.2: pH 7

With 1-hydroxy-7-aza-benzotriazole; piperdinium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In ethanol; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(5Z)-2-{[5-(aminomethyl)-2-chlorophenyl]amino}-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one

N,N-dimethylglycine hydrochoride

N-(3-amino-4-chlorophenylmethyl)carbamic acid t-butyl ester

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