2-(2-chloro-allyl)-N⁴-cyclohexylmethyl-N¹-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide

Base Information

• Chemical Name: 2-(2-chloro-allyl)-N⁴-cyclohexylmethyl-N¹-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide
• CAS No.: 245756-15-4
• Molecular Formula: C₃₈H₅₉ClN₄O₃
• Molecular Weight: 655.364

Synonyms:2-(2-chloro-allyl)-N⁴-cyclohexylmethyl-N¹-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide

Chemical Property of 2-(2-chloro-allyl)-N⁴-cyclohexylmethyl-N¹-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-(2-chloro-allyl)-N⁴-cyclohexylmethyl-N¹-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide

There total 10 articles about 2-(2-chloro-allyl)-N⁴-cyclohexylmethyl-N¹-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide 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: 78.0%

2-<(cyclohexylmethyl)amino>-N-methyl-N-<2-(2-pyridinyl)ethyl>acetamide (192516-54-4) + (S)-5-Chloro-3-((Z)-(S)-1-cyclohexylmethyl-5-methyl-hex-2-enylcarbamoyl)-hex-5-enoic acid (245756-14-3) → 2-(2-chloro-allyl)-N4-cyclohexylmethyl-N1-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N4-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide (245756-15-4)

Guidance literature:

With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo990321x

Reference yield:

betahistine (5638-76-6) → 2-(2-chloro-allyl)-N4-cyclohexylmethyl-N1-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N4-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide (245756-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pivaloyl chloride; Et₃N

2.1: 4N HCl / dioxane

2.2: NaOH

3.1: 78 percent / N-methylmorpholine; TBTU / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; hydrogenchloride; pivaloyl chloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; 1,4-dioxane; 1.1: Substitution / 2.1: Hydrolysis / 2.2: Hydrolysis / 3.1: Acylation;

DOI:10.1021/jo990321x

Reference yield:

dimethyl(2-chloro-2-propenyl)malonate (58404-02-7) → 2-(2-chloro-allyl)-N4-cyclohexylmethyl-N1-(1-cyclohexylmethyl-5-methyl-hex-2-enyl)-N4-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide (245756-15-4)

Guidance literature:

Multi-step reaction with 7 steps

1: BnEt₃NCl; 10N NaOH / H₂O / 20 °C

2: KOH / methanol; H₂O / 20 °C

3: toluene / 20 h / Heating

4: 48 percent / Alcalase / H₂O; acetone / 71 h / pH 7.2 - 8.1

5: 86 percent / TBTU; DIPEA / acetonitrile / 18 h / 20 °C

6: 95 percent / 30 percent HBr / acetic acid / 5 °C

7: 78 percent / N-methylmorpholine; TBTU / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; potassium hydroxide; sodium hydroxide; Alcalase; N-benzyl-N,N,N-triethylammonium chloride; hydrogen bromide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; water; acetic acid; acetone; toluene; acetonitrile; 1: Alkylation / 2: Hydrolysis / 3: Decarboxylation / 4: Hydrolysis / 5: Acylation / 6: Hydrolysis / 7: Acylation;

DOI:10.1021/jo990321x

upstream raw materials:

2-<(cyclohexylmethyl)amino>-N-methyl-N-<2-(2-pyridinyl)ethyl>acetamide

(S)-5-Chloro-3-((Z)-(S)-1-cyclohexylmethyl-5-methyl-hex-2-enylcarbamoyl)-hex-5-enoic acid

betahistine

dimethyl(2-chloro-2-propenyl)malonate

Downstream raw materials:

2-(2-chloro-allyl)-N¹-[2-cyclohexyl-1-(5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-N⁴-cyclohexylmethyl-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide

BILA 2157 BS

2-(2-chloro-allyl)-N⁴-cyclohexylmethyl-N¹-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide

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