N-tert-ButyloxycarbonylaMino KU-0058948

Base Information

• Chemical Name: N-tert-ButyloxycarbonylaMino KU-0058948
• CAS No.: 874116-49-1
• Molecular Formula: C₂₆H₂₉FN₄O₄
• Molecular Weight: 480.539
• Mol file: 874116-49-1.mol

Synonyms:tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepane-1-carboxylate

Chemical Property of N-tert-ButyloxycarbonylaMino KU-0058948

Chemical Property:

• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

N-tert-ButyloxycarbonylaminoKU-0058948 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected KU-0058948 (K660400), a poly (ADP-ribose) polymerase (PARP) inhibitor.

Technology Process of N-tert-ButyloxycarbonylaMino KU-0058948

There total 8 articles about N-tert-ButyloxycarbonylaMino KU-0058948 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: 97.0%

2-fluoro-5-[(4’-oxo-3’H-phthalazin-1’-yl)methyl]benzoic acid (763114-26-7) + tert-butyl 1,4-diazepine-1-carboxylate (112275-50-0) → tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepane-1-carboxylate (874116-49-1)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm8001263

Reference yield:

dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate (61260-15-9) → tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepane-1-carboxylate (874116-49-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 15 - 20 °C

2.1: sodium hydroxide; water / 1 h / 90 °C

2.2: 70 °C

2.3: 20 °C / pH 3 - 4

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 24 h / 20 °C

With water; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

2-fluoro-5-formylbenzonitrile (218301-22-5) → tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepane-1-carboxylate (874116-49-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 15 - 20 °C

2.1: sodium hydroxide; water / 1 h / 90 °C

2.2: 70 °C

2.3: 20 °C / pH 3 - 4

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 24 h / 20 °C

With water; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

2-fluoro-5-[(4’-oxo-3’H-phthalazin-1’-yl)methyl]benzoic acid

tert-butyl 1,4-diazepine-1-carboxylate

o-carboxybenzaldehyde

2-fluoro-5-formylbenzonitrile

Downstream raw materials:

4-[[4-fluoro-3-[(hexahydro-1H-1,4-diazepin-1-yl)carbonyl]phenyl]methyl]-1(2H)-phthalazinone

1-cyclopropyl-2-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl) ethane-1,2-dione

1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1 -yl)methyl)benzoyl)-1 ,4-diazepan-1-yl)-3,3-dimethylbutane-1,2-dione

1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl)-2-phenylethane-1,2-dione

Refernces

• 1、 -. "HETEROCYCLIC DERIVATES，PREPARATION PROCESSES AND MEDICAL USES THEREOF". Page/Page column 26. . Retrieved 2012/06/16.
• 2、 Cockcroft, Xiao-Ling,Dillon, Krystyna J.,Dixon, Lesley,Drzewiecki, Jan,Kerrigan, Frank,Loh Jr., Vincent M.,Martin, Niall M.B.,Menear, Keith A.,Smith, Graeme C.M.. "Phthalazinones 2: Optimisation and synthesis of novel potent inhibitors of poly(ADP-ribose)polymerase". . p. 1040 - 1044. Retrieved 2007/10/03.