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[ CAS No. 942189-39-1 ]

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2D
Chemical Structure| 942189-39-1
Chemical Structure| 942189-39-1
Structure of 942189-39-1 *Storage: {[proInfo.prStorage]}

Quality Control of [ 942189-39-1 ]

Related Doc. of [ 942189-39-1 ]

SDS

Product Details of [ 942189-39-1 ]

CAS No. :942189-39-1MDL No. :MFCD17169854
Formula : C26H18BrN3O2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :484.34Pubchem ID :58946443
Synonyms :

Computed Properties of [ 942189-39-1 ]

TPSA : 63.6 H-Bond Acceptor Count : 3
XLogP3 : 7.2 H-Bond Donor Count : 0
SP3 : 0.04 Rotatable Bond Count : 4

Safety of [ 942189-39-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H320-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 942189-39-1 ]

  • Upstream synthesis route of [ 942189-39-1 ]

[ 942189-39-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 76-83-5 ]
  • [ 5401-94-5 ]
  • [ 942189-39-1 ]
YieldReaction ConditionsOperation in experiment
10%
Stage #1: With bromine In methanol
Stage #2: With sodium hydride In N,N-dimethyl-formamide
(S)-N-(3-(6-isopropoxypyridin-3-yl)- 1H-indazol-5-yl)- 1 -(2-(4-(4-(1 -methyl-1H- 1 ,2,4-triazol-3 -yl)phenyl)-3 , 6-dihydropyridin- 1 (2H)-yl)-2-oxoethyl)-3 -(methylthio)pyrrolidine3-carboxamide free base synthesis is a 19 step process. Compound preparation is divided into three intermediate preparations A, B and C followed by coupling of the intermediates. Allintermediates start with commercially available compounds. Compound 5 is prepared by reaction of the commercially available bromo-4-cyanobenzene with methyl hydrazine under acidic conditions to form the hydrazinoimidate 2 in modest yield. After reaction with formic acid in two steps the bromophenyl-N-methyl triazole intermediate 3 is obtained. The tetrahydropyridine ring is introduced by a Suzuki reaction of the commercially available Bocprotected tetrahydropyridine-boronate to obtain the tricyclic ring system 4. Chloroacetamide 5 is obtained in excellent yield by reaction of the deprotected 4 with chloroacetylchloride. The pyrrolidine core lOa is obtained in good yield in 5 steps starting from commercially available 6. Reaction with thionylchloride gave the thiomethyl olefin 7. Cycloaddition (2+3) gives 8 followed by removal of the benzyl protection group to give 9. L-Tartaric acid resolution of thepyrrolidine core gives the pure (5) enantiomer 9 after filtration from methanol. After protection as the Boc derivative and hydrolysis of the methyl ester, 10 is obtained in overall 50percent yield. Compound 17 is obtained from commercially available indazole 11. Bromination at the 3- position of indazole 11 proceeds in excellent yield without chromatography to obtain 12. Suzuki reaction of the bromo compound 12 with 14 gives the nitro indazole 16 after chromatography.Reduction of 16 gives aniline 17 as an oil in quantitative yield without chromatography. The final coupling of the intermediates proceeded by coupling 17 with lOa to obtain 18 in good yield. After deprotection of the Boc and Trityl groups the final coupling with 5 gave (S)-N-(3-(6- isopropoxypyridin-3-yl)- 1H-indazol-5-yl)-1 -(2-(4-(4-(1 -methyl-1H- 1 ,2,4-triazol-3-yl)phenyl)- 3 ,6-dihydropyridin- 1 (2H)-yl)-2-oxoethyl)-3 -(methylthio)pyrrolidine-3 -carboxamide afterchromatography. Final purification is carried out by crystallization from methanol/diethylether.This synthetic route has been conducted on a scale that delivered (S)-N-(3-(6-isopropoxypyridin-3-yl)-1H-indazol-5-yl)- 1 -(2-(4-(4-(1 -methyl-1H- 1 ,2,4-triazol-3-yl)phenyl)-3,6-dihydropyridin-1 (2H)-yl)-2-oxoethyl)-3 -(methylthio)pyrroli dine-3 -carboxamide free base (Compound I).
Reference: [1] Patent: WO2016/100152, 2016, A1. Location in patent: Page/Page column 8; 10
[2] Patent: WO2016/100147, 2016, A1. Location in patent: Page/Page column 5; 8
[3] Patent: WO2017/40362, 2017, A1. Location in patent: Page/Page column 4; 6
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