1175298-09-5|tert-Butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)carbamate| Ambeed

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Quality Control of [ 1175298-09-5 ] Purity: 95% SDS Specification

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Product Details of [ 1175298-09-5 ]

CAS No. :	1175298-09-5
Formula :	C₁₇H₃₀BNO₄
M.W :	323.24
SMILES Code :	O=C(OC(C)(C)C)NC1CC(B2OC(C)(C)C(C)(C)O2)=CCC1
MDL No. :	MFCD12032213
InChI Key :	MFPBSOYHSNYOKC-UHFFFAOYSA-N
Pubchem ID :	57812318

Safety of [ 1175298-09-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1175298-09-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	23
Num. arom. heavy atoms	0
Fraction Csp3	0.82
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	92.7
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	56.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.04
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.62
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.78
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.51
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.99

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.43
Solubility	0.12 mg/ml ; 0.000372 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.9
Solubility	0.0408 mg/ml ; 0.000126 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.6
Solubility	0.0821 mg/ml ; 0.000254 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.11 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	4.55

Application In Synthesis of [ 1175298-09-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1175298-09-5 ]

[ 1175298-09-5 ] Synthesis Path-Downstream 1~35

1
[ 958230-19-8 ]
[ 1175298-09-5 ]
tert-butyl (3-(5-formyl-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 14h;	[0302] 1,4-Dioxane (20 mL), a 2 M aqueous solution of sodium carbonate (6 mL) and Pd(PPh3)4 (318 mg) were addedto 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.00 g) and the compound of Reference Example 1(2a) (1.96 g),and the temperature of the obtained mixture was then increased to 100C, followed by stirring for 14 hours. Thereafter,water was added to the reaction mixture for dilution, and the obtained mixture was then extracted with chloroform. Thegathered organic layer was washed with a saturated saline, dried over anhydrous sodium sulfate, and then concentratedunder a reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform : methanol) toobtain a product of interest (1.70 g, yield: 91%).ESI-MS m/z 342(MH+)

References: [1]Patent: EP3070086,2016,A1 .Location in patent: Paragraph 0302.

2
[ 1175298-09-5 ]
4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde [ No CAS ]
tert-butyl (3-(3-formyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 14h;Inert atmosphere;	[0353] 1,4-Dioxane (15 mL) and a 2 M aqueous solution of sodium carbonate (4.5 mL) were added to the Compound48(1) (1.4 g), the compound of Reference Example 1(2a) (2.19 g) and Pd(PPh3)4 (520 mg). Under a nitrogen atmosphere,the mixture was stirred at 90C for 14 hours. Thereafter, water was added to the reaction mixture, and the obtainedmixture was then extracted with ethyl acetate. The gathered organic layer was washed with a saturated saline, driedover anhydrous sodium sulfate, and then concentrated under a reduced pressure. The obtained residue was purifiedby silica gel chromatography (hexane : ethyl acetate) to obtain a product of interest (1.78 g, yield: 84%).1H NMR(CDCl3) delta: 10.06 (s, 1H), 8.35 (d, J=4.8 Hz, 1H), 8.09 (s, 1H), 7.03 (d, J=4.8 Hz, 1H), 5.81 (s, 1H), 5.74 (s, 2H),5.37 (br. s., 1H), 4.10 - 4.02 (m, 1H), 3.61 (dd, J=7.7, 8.8 Hz, 2H), 2.82 - 2.65 (m, 1H), 2.47 - 2.21 (m, 3H), 1.98 - 1.76(m, 2H), 1.47 (s, 9H), 0.98 - 0.89 (m, 2H), -0.03 (s, 6H)ESI-MS m/z 472(MH+)

References: [1]Patent: EP3070086,2016,A1 .Location in patent: Paragraph 0353.

3
(S)-5-((tert-butoxycarbonyl)amino)cyclohex-1-en-1-yl trifluoromethanesulfonate [ No CAS ]
[ 73183-34-3 ]
[ 1175298-09-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; at 80℃; for 14h;Inert atmosphere;	[0249] DMF (90 mL) was added to the compound of Reference Example 1(1a) (9.25 g), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (10.2 g) and potassium acetate (3.95 g), followed by nitrogen substitution. Thereafter,PdCl2(dppf)CH2Cl2 (980 mg) was added to the resultant, and the obtained mixture was then stirred at 80C for 14 hours.Thereafter, the reaction mixture was cooled to a room temperature, and ethyl acetate and water were then added to themixture. Thereafter, thus obtained mixture was filtered through Celite. The filtrate was extracted with ethyl acetate, andthereafter, the gathered organic layer was washed with water and then with a saturated saline. The resultant was driedover anhydrous sodium sulfate, and then concentrated under a reduced pressure. The obtained residue was purifiedby silica gel chromatography (hexane : ethyl acetate) to obtain a product of interest (6.51 g, yield: 75%).1H NMR(CDCl3) delta: 6.56 - 6.51 (m, 1H), 4.58 - 4.41 (m, 1H), 3.80 - 3.62 (m, 1H),2.58 - 2.41 (m, 1H), 2.31 - 2.13 (m, 2H),1.98 - 1.77 (m, 2H), 1.54 - 1.47 (m, 1H), 1.44 (s, 9H), 1.25 (s, 12H)ESI-MS m/z 324 (MH+)

References: [1]Patent: EP3070086,2016,A1 .Location in patent: Paragraph 0249.

4
[ 1175298-09-5 ]
tert-butyl (3-(5-formyl-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

5
[ 1175298-09-5 ]
tert-butyl (3-(5-formyl-3-(furan-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

6
[ 1175298-09-5 ]
tert-butyl [3-(3-(furan-2-yl)-5-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl]carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

7
[ 1175298-09-5 ]
N-(3-(3-(furan-2-yl)-5-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)acrylamide [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

8
[ 1175298-09-5 ]
tert-butyl (3-(3-(1,2,4-oxadiazol-5-yl)-1-tosyl-1H-pyrrolo [2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

9
[ 1175298-09-5 ]
tert-butyl (3-(3-(oxazol-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

10
[ 1175298-09-5 ]
4-(5-((tert-butoxycarbonyl)amino)cyclohex-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

11
[ 1175298-09-5 ]
tert-butyl (3-(3-(hydrazinecarbonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

12
[ 1175298-09-5 ]
tert-butyl (3-(3-(1,3,4-oxadiazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

13
[ 1175298-09-5 ]
N-(3-(3-(1,3,4-oxadiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)acrylamide [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

14
[ 1175298-09-5 ]
tert-butyl (3-(3-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

15
[ 1175298-09-5 ]
tert-butyl (3-(3-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

16
[ 1175298-09-5 ]
tert-butyl (3-(3-(1,3,4-thiadiazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

17
[ 1175298-09-5 ]
N-(3-(3-(1,3,4-thiadiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)acrylamide [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

18
[ 1175298-09-5 ]
tert-butyl (3-(5-formyl-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-yl)cyclohex-3en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

19
[ 1175298-09-5 ]
4-(5-((tert-butoxycarbonyl)amino)cyclohex-1-en-1-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

20
[ 1175298-09-5 ]
C₂₀H₂₃N₅O₃ [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

21
[ 1175298-09-5 ]
C₂₆H₃₉N₅O₅Si [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

22
[ 1175298-09-5 ]
C₂₀H₂₃N₅O₂S [ No CAS ]

References: [1]Patent: EP3070086,2016,A1 .

23
[ 1175298-09-5 ]
[ 98-59-9 ]
[ 348640-06-2 ]
tert-butyl (3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl) cyclohex-3-en-1-yl) carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		[0258] To 4-bromo-1H-pyrrolo[2,3-b]pyridine (2.00 g), the compound of Reference Example 1(2a) (4.60 g) and tripotassiumphosphate (5.41 g), 1,4-dioxane (20 mL) and water (3.3 mL) were added, followed by nitrogen substitution, andPdCl2(dppf)CH2Cl2 (746 mg) was then added to the reaction mixture. Thus obtained mixture was stirred at 100C for 5hours. Thereafter, the reaction mixture was cooled to a room temperature, and ethyl acetate and water were then addedto the mixture. Thereafter, thus obtained mixture was filtered through Celite. The filtrate was then extracted with ethylacetate, and the gathered organic layer was then washed with water and then with a saturated saline. The resultant wasdried over anhydrous sodium sulfate, and then concentrated under a reduced pressure. The obtained residue waspurified by silica gel chromatography (chloroform : methanol) to obtain a corresponding coupling product. The obtainedcoupling product was subjected to the subsequent reaction without further purification.[0259] DMF (30 mL) was added to the obtained coupling product, and the obtained mixture was then cooled to 0C.Subsequently, N-iodosuccinimide (2.52 g) was added to the mixture, and the obtained mixture was then stirred at 0Cfor 30 minutes. Thereafter, a 0.5 M aqueous solution of sodium hydrogen sulfite was added to the reaction mixture, andthe obtained mixture was then extracted with ethyl acetate. The gathered organic layer was washed with water and thenwith a saturated saline. The resultant was dried over anhydrous sodium sulfate, and then concentrated under a reducedpressure. The obtained residue was purified by silica gel chromatography (chloroform : methanol) to obtain a correspondingiodine product. The obtained iodine product was subjected to the subsequent reaction without further purification.[0260] DMF (30 mL) was added to the obtained iodine product, and the obtained mixture was then cooled to 0C.Thereafter, 60% sodium hydride (1.02 g), and then, para-toluenesulfonyl chloride (2.33 g) were added to the reactionmixture, and the obtained mixture was then stirred at 0C for 30 minutes. Thereafter, ice water was added to the reactionmixture, and the water layer was then extracted with ethyl acetate. The gathered organic layer was washed with waterand then with a saturated saline. The resultant was dried over anhydrous sodium sulfate, and then concentrated undera reduced pressure. The obtained residue was purified by silica gel chromatography (hexane : ethyl acetate) to obtaina product of interest (3.49 g, yield: 58%).1H NMR (CDCl3) delta: 8.35 (d, J=4.9 Hz, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.89 (s, 1H), 7.30 (d, J=8.5 Hz, 2H), 6.94 (d, J=4.9Hz, 1H), 5.72 - 5.67 (m, 1H), 4.75 - 4.59(m, 1H), 4.11 - 3.97 (m, 1H), 2.70 - 2.60 (m, 1H), 2.40 - 2.32 (m, 2H), 2.39 (s,3H), 2.22 - 2.09 (m, 1H), 2.04 - 1.94 (m, 1H), 1.75 - 1.62 (m, 1H), 1.44 (s, 9H)ESI-MS m/z 594(MH+)

References: [1]Patent: EP3070086,2016,A1 .Location in patent: Paragraph 0258.

24
[ 1175298-09-5 ]
4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde [ No CAS ]
tert-butyl (3-(3-formyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 10h;Inert atmosphere;	[0347] 1,4-Dioxane (44 mL) and a 2 M aqueous solution of sodium carbonate (6.57 mL) were added to the Compound47(1) (2.20 g), the compound of Reference Example 1(2a) (2.34 g) and Pd(PPh3)4 (1.14 mg), followed by nitrogensubstitution. Thereafter, the reaction mixture was stirred at 100C for 10 hours. Thereafter, water was added to thereaction mixture, and the obtained mixture was then extracted with ethyl acetate. The gathered organic layer was washedwith a saturated saline, dried over anhydrous sodium sulfate, and then concentrated under a reduced pressure. Theobtained residue was purified by silica gel chromatography (hexane: ethyl acetate) to obtain a product of interest (2.05g, yield: 63%).ESI-MS m/z 496(MH+)

References: [1]Patent: EP3070086,2016,A1 .Location in patent: Paragraph 0347.

25
tert-butyl N-[(1S)-3-oxocyclohexyl]carbamate [ No CAS ]
[ 1175298-09-5 ]

References: [1]Patent: EP3070086,2016,A1 .

26
[ 885280-38-6 ]
[ 1175298-09-5 ]

References: [1]Patent: EP3070086,2016,A1 .
[2]Patent: EP3330271,2018,A1 .

27
5-((tert-butoxycarbonyl)amino)cyclohex-1-en-1-yl trifluoromethanesulfonate [ No CAS ]
[ 73183-34-3 ]
[ 1175298-09-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; at 80℃; for 14h;Inert atmosphere;	DMF (90 mL) was added to the compound (9.25 g) of Reference Example 1(1a), 4, 4, 4?, 4?, 5, 5, 5?, 5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (10.2 g) and potassium acetate (3.95 g), followed by nitrogen substitution. Thereafter,PdCl2(dppf)CH2Cl2 (980.mg) was added to the resultant, and the obtained mixture was then stirred at 80C for 14 hours.Thereafter, the reaction mixture was cooled to a room temperature, and ethyl acetate and water were then added to themixture. Thereafter, the thus obtained mixture was filtered through Celite. The filtrate was extracted with ethyl acetate,and thereafter, the gathered organic layer was washed with water and then with a saturated saline. The resultant wasdried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. The obtained residue waspurified by silica gel chromatography (hexane : ethyl acetate) to obtain a product of interest (6.51 g, yield: 75%).1H NMR(CDCl3) delta: 6.56 - 6.51 (m, 1H), 4.58 - 4.41 (m, 1H), 3.80 - 3.62 (m, 1H),2.58 - 2.41 (m, 1H), 2.31 - 2.13 (m, 2H),1.98 - 1.77 (m, 2H), 1.54 - 1.47 (m, 1H), 1.44 (s, 9H), 1.25 (s, 12H)ESI-MS m/z 324(MH+)

References: [1]Patent: EP3330271,2018,A1 .Location in patent: Paragraph 0111; 0112.

28
[ 1175298-09-5 ]
(E)-N-(3-(5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)but-2-enamide [ No CAS ]

References: [1]Patent: EP3330271,2018,A1 .

29
[ 1175298-09-5 ]
C₁₇H₂₁IN₄O₂ [ No CAS ]

References: [1]Patent: EP3330271,2018,A1 .

30
[ 1175298-09-5 ]
tert-butyl (3-(5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3330271,2018,A1 .

31
[ 1175298-09-5 ]
tert-butyl (3-(5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3330271,2018,A1 .

32
[ 1175298-09-5 ]
N-(3-(5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)acrylamide [ No CAS ]

References: [1]Patent: EP3330271,2018,A1 .

33
[ 1175298-09-5 ]
tert-butyl (3-(5-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

References: [1]Patent: EP3330271,2018,A1 .

34
[ 1175298-09-5 ]
N-(3-(5-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)acrylamide [ No CAS ]

References: [1]Patent: EP3330271,2018,A1 .

35
[ 1175298-09-5 ]
[ 3680-69-1 ]
tert-butyl (3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 14h;Inert atmosphere;	To 4-chloro-7H-pyrrolo[2,3-d]pyrimidin (2.97 g), the compound (9.39 g) of Reference Example 1(2a) and tripotassiumphosphate (10.2 g), 1,4-dioxane (66 mL) and water (11 mL) were added, followed by nitrogen substitution, andPdCl2(dppf)CH2Cl2 (1.41 g) was then added to the reaction mixture. The thus obtained mixture was stirred at 100C for14 hours. Thereafter, the reaction mixture was cooled to a room temperature, and ethyl acetate and water were thenadded to the mixture. Thereafter, the thus obtained mixture was filtered through Celite. The filtrate was then extractedwith ethyl acetate, and the gathered organic layer was then washed with water and then with a saturated saline. Theresultant was dried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. The obtainedresidue was purified by silica gel chromatography (chloroform : methanol) to obtain tert-butyl (3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)carbamate. The above obtained compound was used in the subsequent reaction withoutfurther purification.

References: [1]Patent: EP3330271,2018,A1 .Location in patent: Paragraph 0122; 0123.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Halogenation • Heat of Combustion • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 1175298-09-5 ]

Organoborons

A154871 [1251732-64-5]

tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)carbamate

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A207180 [900503-08-4]

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A130704 [286961-14-6]

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A128148 [1121057-77-9]

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A419394 [1356111-39-1]

1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)pyrrolidine

Similarity: 0.78

Alkenyls

A154871 [1251732-64-5]

tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)carbamate

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A207180 [900503-08-4]

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

Similarity: 0.87

A419394 [1356111-39-1]

1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)pyrrolidine

Similarity: 0.78

A272366 [1123661-15-3]

8-(Phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

Similarity: 0.69

A201110 [141091-37-4]

2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.67

Aliphatic Cyclic Hydrocarbons

A154871 [1251732-64-5]

tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)carbamate

Similarity: 0.99

A201110 [141091-37-4]

2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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A148073 [1310384-24-7]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enol

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A168808 [859217-67-7]

2-(4,4-Dimethyl-1-cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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A367400 [859217-85-9]

4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolane

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Amides

A154871 [1251732-64-5]

tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)carbamate

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A207180 [900503-08-4]

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A130704 [286961-14-6]

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A128148 [1121057-77-9]

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A119303 [885693-20-9]

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Amines

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A114471 [330794-35-9]

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate

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A129545 [2126812-29-9]

Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate

Similarity: 0.74

A167667 [330793-01-6]

tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Similarity: 0.69

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CAS No.: 1175298-09-5

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CAS No.: 1175298-09-5

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CAS No.: 1175298-09-5

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CAS No.: 1175298-09-5

Alternative Products

Product Details of [ 1175298-09-5 ]

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Computational Chemistry of [ 1175298-09-5 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 1175298-09-5 ]

[ 1175298-09-5 ] Synthesis Path-Downstream 1~35

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Technical Information

Categories

Related Functional Groups of [ 1175298-09-5 ]

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Alkenyls

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Related Functional Groups of
[ 1175298-09-5 ]