115269-99-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 3845, 1988 DOI: 10.1021/jo00251a035

InChI:InChI=1/C13H23NO4/c1-8-9-14(10(15)17-12(2,3)4)11(16)18-13(5,6)7/h8H,1,9H2,2-7H3

Upstream product

• 591-87-7 Allyl acetate 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 106-95-6 allyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 78888-18-3 N-tert-butoxycarbonylprop-2-en-1-amine 
• 89004-82-0 potassium bis(tert-butoxycarbonyl)amide 
• 34619-03-9 tert-butyldicarbonate 
• 107-11-9 1-amino-2-propene 

Downstream Products

• 115270-07-0 3--1-phenyl-1-propene 
• 1286169-96-7 C₂₇H₃₅NO₆ 
• 1238892-53-9 (3-phenyl-allyl)-carbamic acid di-tert-butyl ester 

Relevant academic research and scientific papers

Syntheses of (Z)- and (E)-4-amino-2-(trifluoromethyl)-2-butenoic acid and their inactivation of γ-aminobutyric acid aminotransferase

(Z)- and (E)-4-amino-2-(trifluoromethyl)-2-butenoic acid (4Scheme 1Proposed mechanism of inactivation of GABA-AT by 1 or 4.Scheme 2Synthesis of 4 and 5. (i) Zn, CO2, DMF; (ii) aq. HCl; (iii) (CH3)2C=CH2, concd H2SO4, CH2Cl2; (iv) KOH, EtOH; (v) allyl bromide, DMF, 100°C; (vi) O3, -78°C, CH2Cl2; (vii) Me2S; (viii) Zn-Cu, Ac2O, 4 A molecular sieves, THF, 66°C; (ix) C18 reversed-phase HPLC; (x) TFA, CH2Cl2; (xi) Dowex 50.Scheme 3Proposed mechanism of inactivation of GABA-AT by 4 with release of activated species. and 5, respectively) were synthesized and investigated as potential mechanism-based inactivators of γ-aminobutyric acid aminotransferase (GABA-AT) in a continuing effort to map the active site of this enzyme. The core α-trifluoromethyl-α,β-unsaturated ester moiety was prepared via a Reformatsky/reductive elimination coupling of the key intermediates tert-butyl 2,2-dichloro-3,3,3-trifluoropropionate and N,N-bis(tert-butoxycarbonyl)glycinal. Both 4 and 5 inhibited GABA-AT in a time-dependent manner, but displayed non-pseudo-first-order inactivation kinetics; initially, the inactivation rate increased with time. Further investigation demonstrated that the actual inactivator is generated enzymatically from 4 or 5. This inactivating species is released from the active site prior to inactivation, and as a result, 4 and 5 cannot be defined as mechanism-based inactivators. Furthermore, 4 and 5 are alternate substrates for GABA-AT, transaminated by the enzyme with K(m) values of 0.74 and 20.5 mM, respectively. Transamination occurs approximately 276 and 305 times per inactivation event for 4 and 5, respectively. The enzyme also catalyzes the elimination of the fluoride ion from 4 and 5. A mechanism to account for these observations is proposed. Copyright (C) 1999 Elsevier Science Ltd.

Evaluation of kilogram-scale Sonagashira, Suzuki, and Heck coupling routes to oncology candidate CP-724,714

The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6- methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetainide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin.

Potent, orally bioavailable somatostatin agonists: Good absorption achieved by urea backbone cyclization

Backbone cyclization of urea-based somatostatin agonists resulted in novel, orally bioavailable agonists. Binding assays confirmed that the resulting conformationally constrained cyclic ureas retained the potency of their acycyclic counterparts. SAP, studies subsequently led to highly potent analogs, selective for receptor subtype 2, and having good oral bioavailability.

NITROGENOUS HETEROCYCLIC COMPOUND, PREPARATION METHOD, INTERMEDIATE, COMPOSITION, AND APPLICATION

A nitrogenous heterocyclic compound, a preparation method, an intermediate, a composition, and an application. The present invention provides a nitrogenous heterocyclic compound as represented by formula I, pharmaceutically acceptable salts thereof, enantiomers thereof, diastereoisomers thereof, tautomers thereof, solvates thereof, metabolites thereof, or prodrugs thereof. The compound has high inhibitory activity against ErbB2 tyrosine kinase, has good inhibitory activity against human breast cancer cells BT-474, human gastric cancer cells NCI-N87 and the like with high expression of ErbB2, and in addition has relatively weak inhibitory activity against EGFR kinase, that is, the compound is an EGFR/ErbB2 double target inhibitor that attenuates EGFR kinase inhibitory activity or a small-molecule inhibitor having selectivity for an ErbB2 target. (I)

NITROGENOUS HETEROCYCLIC COMPOUND, PREPARATION METHOD, INTERMEDIATE, COMPOSITION AND USE

Disclosed are a nitrogenous heterocyclic compound, intermediates, a preparation method, a composition and use thereof. The nitrogenous heterocyclic compound in the present invention is as shown in formula I. The compound has a high inhibitory activity towards ErbB2 tyrosine kinase and a relatively good inhibitory activity towards human breast cancer BT-474 and human gastric cancer cell NCI-N87 which express ErbB2 at a high level, and at the same time has a relatively weak inhibitory activity towards EGFR kinase. Namely, the compound is a highly selective small-molecule inhibitor targeted at ErbB2, and hence it has a high degree of safety, and can effectively enlarge the safety window in the process of taking the drug.

Substrate-directable heck reactions with arenediazonium salts. The regio- and stereoselective arylation of allylamine derivatives and applications in the synthesis of naftifine and abamines

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Synthesis of a platform to access bistramides and their analogues

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Rhodium-catalyzed asymmetric hydroformylation of n-allvlamides: Highly enantioselective approach to β2-amino aldehydes

(Figure Presented) You're having a lahf I The asymmetric hydroformylation (AHF) of allylic compounds, catalyzed by a rhodium-yanphos complex, is a direct and concise route to ss2-amino aldehydes, acids, and alcohols with excellent enantioselectivity (see scheme; TON =turnover number, acac = acetylacetonate).

PROCESSES FOR THE PREPARATION OF N-((((PYRIDINYLOXY) -PHENYLAMINO) QUINAZOLINYL)- ALLYL) ACETAMIDE DERIVATIVES AND RELATED COMPOUNDS AS WELL AS INTERMEDIATES OF SUCH PROCESSES AND PROCESSES FOR THE PREPARATION OF SUCH INTERMEDIATES

The invention relates to processes for preparing compounds of the formula (1) and to pharmaceutically acceptable salts, prodrugs and solvates thereof, wherein R1, R3, R4, R6 R11, R13 R14 R15, R16, R17, k, I, and m are as defined herein. The present invention also relates to intermediates represented by the formula (3a) wherin R4, and R5 are independently selected from hydrogen and C1-C6alkyl; each R13, R14, R15 and R16 is independently selected from hydrogen, C1-C6alkyl and CH2OH, R17 and R18 are independently C1-C6 alkyl, and k and I are independently an integer from 1 to 3, as well as to a process for preparing these intermediates.

2-Methyltetrahydrofuran as an Alternative to Dichloromethane in 2-Phase Reactions

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