5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Base Information

• Chemical Name: 5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide
• CAS No.: 1046469-42-4
• Molecular Formula: C₂₁H₂₃ClFN₃O₃
• Molecular Weight: 419.883

Synonyms:5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Chemical Property of 5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

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Technology Process of 5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

There total 2 articles about 5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide 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: 79.0%

5-[3-(2-chloro-4-fluorophenyl)-3-oxopropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (1046469-41-3) → 5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (1046469-42-4)

Guidance literature:

5-[3-(2-chloro-4-fluorophenyl)-3-oxopropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide; With potassium tert-butylate; RuCI₂[(S)-Xyl-P-Phos][(S)-DAIPEN]; In isopropyl alcohol; tert-butyl alcohol; at 50 ℃;

With hydrogen; In isopropyl alcohol; tert-butyl alcohol; at 70 ℃; for 20h; under 60006 Torr; autoclave;

Reference yield:

5-[3-(2-chloro-4-fluorophenyl)-3-oxopropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (1046469-41-3) → 5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (1046469-42-4) + 5-[(3S)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Guidance literature:

With RuCl₂[(S)-Xyl-P-Phos][(S)-DAIPEN]; potassium tert-butylate; hydrogen; In isopropyl alcohol; tert-butyl alcohol; at 50 - 80 ℃; under 60006 Torr; optical yield given as %ee; Inert atmosphere; Autoclave;

DOI:10.1021/jm100040c

Reference yield: 91.0%

5-[(3R)-3-(2-chloro-4-fluorophenyl)-3-hydroxypropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (1046469-42-4) → (8S)-8-(2-chloro-4-fluorophenyl)-N,N,2,3-tetramethyl-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxamide (1046469-43-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h;

upstream raw materials:

5-[3-(2-chloro-4-fluorophenyl)-3-oxopropyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Downstream raw materials:

(8S)-8-(2-chloro-4-fluorophenyl)-N,N,2,3-tetramethyl-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxamide

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