135908-33-7|Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate| Ambeed

Structure of 135908-33-7

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Quality Control of [ 135908-33-7 ] Purity: 95% SDS Specification

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Product Details of [ 135908-33-7 ]

CAS No. :	135908-33-7
Formula :	C₁₀H₁₇NO₂
M.W :	183.25
SMILES Code :	O=C(C1(CC2)CCC2(N)CC1)OC
MDL No. :	MFCD20693756
InChI Key :	HDIKFAFEMDBXOS-UHFFFAOYSA-N
Pubchem ID :	53426661

Safety of [ 135908-33-7 ]

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

Computational Chemistry of [ 135908-33-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	0
Fraction Csp3	0.9
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	49.73
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.13
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	0.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.21
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.	1.31
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	1.57
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.35

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.18
Solubility	12.0 mg/ml ; 0.0654 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.21
Solubility	11.3 mg/ml ; 0.0616 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-1.79
Solubility	2.95 mg/ml ; 0.0161 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	No
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.	-7.03 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	1.0
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	0.0 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<1.0
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)	3.15

Application In Synthesis of [ 135908-33-7 ]

* 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 [ 135908-33-7 ]

[ 135908-33-7 ] Synthesis Path-Downstream 1~55

1
[ 135908-33-7 ]
[ 910789-89-8 ]
4-[2-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-3-methoxycarbonyl-3-methyl-butylamino]-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 3963 - 3966.

2
[ 135908-33-7 ]
[ 910789-89-8 ]
[ 910789-99-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5555 - 5560.

3
[ 135908-33-7 ]
[ 868604-86-8 ]
[ 914618-84-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.

4
[ 862501-91-5 ]
[ 135908-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;20 % Pd(OH)2/C; In methanol; at 20℃; for 1h;	Preparation of Bicyclic Amine 2 (BA-2) methyl 4-aminobicyclo[2.2.2]octane-1-carboxylateTo a solution of methyl 4-[(benzyloxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate (BAI-6, 951 mg, 3 mmol) in methanol (50 mL) was added Pd(OH)2/C (100 mg). Hydrogen gas was bubbled through the stirred reaction mixture for 1 hour at room temperature. After filtration, the filtrate was concentrated to give the titled compound. 1H NMR (400 MHz, CDCl3) delta ppm 3.64 (s, 3H), 1.841.88 (m, 6H), 1.73 (s, 2H), 1.531.57 (m, 6H); LCMS (ESI+) m/z 184 (M+H)+.

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.
[2]Patent: US2010/267738,2010,A1 .Location in patent: Page/Page column 33.

5
[ 135908-33-7 ]
[ 882-09-7 ]
[ 914619-02-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.

6
[ 135908-33-7 ]
4-[2-(4-chloro-phenoxy)-2-methyl-propionylamino]-bicyclo[2.2.2]octane-1-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.

7
[ 135908-33-7 ]
4-[2-(4-chloro-phenoxy)-2-methyl-propionylamino]-bicyclo[2.2.2]octane-1-carboxylic acid amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.

8
[ 135908-33-7 ]
4-{2-methyl-2-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-propionylamino}-bicyclo[2.2.2]octane-1-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.

9
[ 135908-33-7 ]
4-{2-methyl-2-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-propionylamino}-bicyclo[2.2.2]octane-1-carboxylic acid amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.

10
[ 18720-35-9 ]
[ 135908-33-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5408 - 5413.

11
[ 135908-33-7 ]
4′-(tert butyl)-[1,1′-biphenyl]-2-carboxylic acid [ No CAS ]
[ 1048367-68-5 ]

Yield	Reaction Conditions	Operation in experiment
27%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	A mixture containing methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (298mg, 1.63 mmol), 4'-tert-butylbiphenyl-2-carboxylic acid (414 mg, 1.63 mmol), DMAP (227 mg, 1.86 mmol) and EDC HCl (470 mg, 2.45 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by chromatography (elution = 16:1 petrolueum ether/EtOAc) to afford methyl 4-(4'-fcrt-butylbiphenyl-2- ylcarboxamido)bicyclo[2.2.2]octane-l -carboxylate as an off-white solid (186 mg, yield: 27%). 1H NMR (400 MHz, CDCl3): delta 7.74 (IH, d, J= 6.4 Hz), 7.48-7.39 (4H, m), 7.35- 7.31 (3H, m), 4.77 (IH, s), 3.62 (3H, s), 1.79-1.75 (6H, m), 1.62-1.58 (6H, m), 1.36 (9H, s).

References: [1]Patent: WO2008/100423,2008,A1 .Location in patent: Page/Page column 124.

12
methyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]
[ 135908-33-7 ]

Yield	Reaction Conditions	Operation in experiment
12%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 760.051 Torr; for 48h;	In a typical run, methyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-l- carboxylate (2.14 g, 14.1 mmol) was taken up in MeOH (50 mL) along with 10% Pd on C (300 mg) and flushed thoroughly with nitrogen. The reaction mixture was stirred at room temperature under 1 atm of hydrogen for 2 days. The mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The crude product was taken up in CH2Cl2 and extracted with dilute 1 N HCl. The combined aqueous layers were neutralized with NaHCO3 and then extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford methyl 4- aminobicyclo[2.2.2]octane-l -carboxylate as an oil (298 mg, yield: 12%). 1H NMR (400 MHz, DMSO): delta 3.59-3.54 (3H, m), 1.74-1.68 (6H, m), 1 .39-1.34 (6H, m).

References: [1]Patent: WO2008/100423,2008,A1 .Location in patent: Page/Page column 123.

13
[ 135908-33-7 ]
[ 1252672-46-0 ]
C₂₁H₂₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 100℃; for 5h;Neat (no solvent); Inert atmosphere;	Example 874-[N-cyano-2-methyl-2-phenoxypropanimidoyl]amino}bicyclo[2.2.2]octane-1-carboxylic acidEthyl N-cyano-2-methyl-2-phenoxypropanimidoate (CI-1) (1 mmol) and <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong> (BA-2) (1 mmol) were mixed, and the neat mixture was heated to 100 C. under nitrogen and stirred for 5 hours. After cooling, the mixture was purified by column chromatography on silica gel (mobile phase:CH2Cl2/CH3OH=50/1) to give an impure ester product which was dissolved in methanol (10 mL). To the solution was added a solution of LiOH (10 mg) in methanol (40 mL) and water (1 mL). The mixture was refluxed overnight. After removal of the solvent, the residue was dissolved in water and adjusted pH=56 with HCl (1 mol/L), extracted with ethyl acetate (50 mL×3). The combined extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative reverse phase HPLC [Waters 2767; Benetnach 10-C18 20×250 mm, 10 mum; 35-60% acetonitrile/water (0.05% trifluoroacetic acid), 30 mL/minute; detection at 214 and 254 nm] to give the titled compound.

References: [1]Patent: US2010/267738,2010,A1 .Location in patent: Page/Page column 52.

14
[ 135908-33-7 ]
[ 6542-76-3 ]
[ 1379000-33-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3467 - 3472.

15
[ 135908-33-7 ]
[ 1266116-57-7 ]
[ 1544657-78-4 ]

References: [1]Patent: WO2014/18891,2014,A1 .

16
[ 135908-33-7 ]
[ 1266116-57-7 ]
[ 1544662-43-2 ]

Yield	Reaction Conditions	Operation in experiment
20%		General procedure: Example 69: 4-(((6-((trans-4-(tert-butyl)cyclohexyl)oxy)quinolin-2-yl)methyl)amino)bicyclo[2.2.2] octane-l-carboxylic acid Step 1: methyl 4-(((6-((trans-4-(tert-butyl cyclohexyl oxy quinolin-2-yl methyl amino bicyclor2.2.21oct ane- 1 -carboxylate 2) NaBH(OAc)3 (3 eq), it, 1 h Y: 30% The solution of 6-((trans-4-(tert-butyl)cyclohexyl)oxy)quinoline-2-carbaldehyde (200 mg, 0.6 mmol) and methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (142 mg, 0.644 mmol) in Ethanol (2 mL, 30 mmol) was heated to reflux for 2h. The yellow solution was cooled to room temperature and sodium cyanoborohydride (48.6 mg, 0.773 mmol) was added and was heated to reflux for lh. After cooled down to room temperature, citric acid was added and concentrated down. The solid was suspended in water and filtrate, and the collected solid was washed thoroughly with water. HPLC purification of the solid give the product (62.7 mg, 20%). LCMS Rt = 1.67 min, m/z = 479.30 [M+l]. Lithium hydroxide (15.7 mg, 0.655 mmol) was added to a solution of 4-{ [6-(trans-4-tert-Butyl-cyclohexyloxy)-quinolin-2-ylmethyl]-amino}-bicyclo[2.2.2]octa ne-l-carboxylic acid methyl ester (62.7 mg, 0.131 mmol) in tetrahydrofuran (0.8 mL, 10 mmol) and methanol (0.8 mL, 20 mmol). The mixture was stirred at 50 C overnight, the solvent was concentrated. The residue was taken up in DMSO and cone. HCl (200 uL) was added to solubilize. Purification by preparative HPLC gave the product as a white solid (63 mg, 20%). LCMS (100%, RT=1.57 min, m/z=465.30. 1H NMR (400 MHz, METHANOL-d4) delta ppm 0.94 (s, 9 H) 1.06 - 1.60 (m, 5 H), 1.86 - 1.99 (m, 2H), 2.00- 2.10 (m, 12 H), 2.24 - 2.37 (m, 2 H) 4.32 - 4.46 (m, 1 H) 4.49 (s, 2 H) 7.34 (d, J=2.51 Hz, 1 H) 7.42 (dd, J=9.29, 2.76 Hz, 1 H), 7.47 (d, J=8.53 Hz, 1 H) 8.01 (d, J=9.29 Hz, 1 H) 8.28 (d, J=8.28 Hz, 1 H). Step 2: 4-(((6-((trans-4-(tert-butyl)cvclohexyl)oxy)quinolin-2-yl)methyl)amino)bicyclor2.2.21oct ane-l-carboxylic acid Lithium hydroxide (15.7 mg, 0.655 mmol) was added to a solution of 4-{ [6-(trans-4-tert-butyl-cyclohexyloxy)-quinolin-2-ylmethyl]-amino}-bicyclo[2.2.2]octa ne-l-carboxylic acid methyl ester (62.7 mg, 0.131 mmol) in tetrahydrofuran (0.8 mL, 10 mmol) and methanol (0.8 mL, 20 mmol). The mixture was stirred at 50 C overnight, the solvent was concentrated. The residue was taken up in DMSO and cone. HCl (200 uL) was added to solubilize. Purification by preparative HPLC gave the product as a white solid (2.3 mg, 4%). LCMS (100%, RT=1.57 min, m/z=465.30. 1H NMR (400 MHz, METHANOL-d4) delta ppm 0.94 (s, 9 H) 1.06 - 1.60 (m, 5 H), 1.86 - 1.99 (m, 2H), 2.00- 2.10 (m, 12 H), 2.24 - 2.37 (m, 2 H) 4.32 - 4.46 (m, 1 H) 4.49 (s, 2 H) 7.34 (d, J=2.51 Hz, 1 H) 7.42 (dd, J=9.29, 2.76 Hz, 1 H), 7.47 (d, J=8.53 Hz, 1 H) 8.01 (d, J=9.29 Hz, 1 H) 8.28 (d, J=8.28 Hz, 1 H).

References: [1]Patent: WO2014/18891,2014,A1 .Location in patent: Page/Page column 137; 138.

17
[ 135908-33-7 ]
[ 78119-82-1 ]
[ 1544661-78-0 ]

Yield	Reaction Conditions	Operation in experiment
80%		General procedure: Example 1: 4-(((6-(cyclohexyloxy)naphthalen-2-yl)methyl)amino) bicyclo[2.2.2]octane-l-carboxylic acid Step 1: 4-(((6-hvdroxynaphthalen-2-yl methyl amino bicvclor2.2.21octane-l-carboxylate 6-hydroxy-2-naphthaldehyde (520 mg, 3.02 mmol, 1.0 eq) and methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (663 mg, 3.62 mmol, 1.2 eq) were dissolved in toluene (100 mL). Magnesium sulfate (72 mg, 0.60 mmol, 0.2 eq) was added to the solution and refluxed for 48 h. The solvent was removed in vacuo. The residue was dissolved in THF (150 mL) and sodium cyanoborohydride (571 mg, 9.06 mmol, 3.0 eq) was added. The mixture was refluxed for 24 h. The solvent was removed in vacuo. Water (50 mL) was added to the residue and extracted with EtOAc (2x150 mL). The combined organic phase was washed with brine and dried over Na2S04. The organic phase was concentrated to give methyl 4-(((6-hydroxynaphthalen-2-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylate as yellow solid (819 mg, Y: 80%). ESI-MS (M+H)+: 340.2. 1H NMR (400 MHz, DMSO-d6) delta: 9.98 (s, 1H), 8.91 (br, 1H), 7.89 (s, 1H), 7.77 (d, / = 9.2 Hz, 1H), 7.75 (d, / = 8.4 Hz, 1H), 7.47 (dd, /= 8.4, 1.6 Hz, 1H), 7.15 (s, 1H), 7.14 (dd, /= 8.0, 2.4 Hz, 1H), 4.17 (s, 2H), 3.60 (s, 3H), 1.91-1.87 (m, 12H). Step 2: 4-(((6-(cvclohexyloxy naphthalen-2-yl methyl amino bicvclor2.2.21octane-l-carboxylic acid Methyl 4-(((6-hydroxynaphthalen-2-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylate (100 mg, 0.295 mmol, 1.0 eq), cyclohexyl methanesulfonate (100 mg, 0.885 mmol, 3.0 eq) and sodium hydroxide (35 mg, 0.875 mmol, 3.0 eq) were dissolved in DMF (2 mL). The mixture was stirred at 100 C for 2 h. After cooling to rt, 1 N HCl was added to adjust pH = 6-7 and extracted with DCM (2x40 mL). The organic phase was washed with brine and dried over Na2S04. After filtration and concentration, the residue was purified by prep-HPLC (65% MeOH/H20) to give 4-(((6-(cyclohexyloxy)naphthalen-2-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylic acid as a white solid (40 mg, yield: 33% in two steps). ESI-MS (M+H)+: 408.2. 1H NMR (400 MHz, CD3OD) delta: 7.89 (s, 1H), 7.84 (d, /= 8.4 Hz, 1H), 7.81 (d, /= 8.8 Hz, 1H), 7.49 (dd, /= 8.8, 2.0 Hz, 1H), 7.28 (d, / = 2.0 Hz, 1H), 7.20 (dd, / = 8.8, 2.4 Hz, 1H), 4.52-4.48 (m, 1H), 4.24 (s, 2H), 2.04-1.99 (m, 14H), 1.86-1.83 (m, 2H), 1.63-1.47 (m, 6H).

References: [1]Patent: WO2014/18891,2014,A1 .Location in patent: Page/Page column 86; 87; 144-145.

18
[ 135908-33-7 ]
[ 1544658-04-9 ]

References: [1]Patent: WO2014/18891,2014,A1 .

19
[ 135908-33-7 ]
[ 1544662-52-3 ]

References: [1]Patent: WO2014/18891,2014,A1 .

20
[ 135908-33-7 ]
[ 1544656-13-4 ]

References: [1]Patent: WO2014/18891,2014,A1 .

21
[ 135908-33-7 ]
[ 1544661-82-6 ]

References: [1]Patent: WO2014/18891,2014,A1 .

22
[ 135908-33-7 ]
[ 1544655-85-7 ]

References: [1]Patent: WO2014/18891,2014,A1 .

23
[ 135908-33-7 ]
[ 1266115-60-9 ]
[ 1544662-66-9 ]

Yield	Reaction Conditions	Operation in experiment
59%		Example 82: 4-(((6-((trans-4-(tert-butyl)cyclohexyl)oxy)naphthalen-2-yl)methyl)amino)bicyclo[2.2 .2]octane-l-carboxylic acid Step 1: 4-{ r6-(trans-4-tert-Butyl-cyclohexyloxy)-naphthalen-2-ylmethyll-amino\|-bicyclor2.2.21o ctane-l-carboxylic acid methyl ester A solution of 6-(4-tert-Butyl-cyclohexyloxy)-naphthalene-2-carbaldehyde (238 mg, 0.767 mmol) (WO 2011/017561 Al) and methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (168 mg, 0.767 mmol) (Prime Organics) in Ethanol (2 mL, 30 mmol) was heated to reflux for 2h. The yellow solution was cooled to room temperature and Sodium cyanoborohydride (57.8 mg, 0.920 mmol) was added and heated to reflux for 3d. The mixture was cooled and concentrated. The solid was suspended in aqueous NaHC03 and EtOAc, The organic layer was washed with brine, dried and concentrated. Column chromatography in Silica gel with MeOH/DCM gives a solid as the product (217mg, 59% yield). LCMS: Rt = 1.69 min m/z 478.30 [M+l]. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.88 - 0.95 (m, 9 H) 1.02 - 1.35 (m, 9 H) 1.35 - 1.54 (m, 2 H) 1.60 - 1.73 (m, 6 H) 1.75 - 1.87 (m, 6 H) 1.90 (d, J=12.99 Hz, 2 H) 2.27 (d, J=11.67 Hz, 2 H) 3.66 (s, 3 H) 3.85 (s, 2 H) 4.17 - 4.35 (m, 1 H) 7.02 - 7.17 (m, 2 H) 7.39 (d, J=8.41 Hz, 1 H) 7.61 - 7.78 (m, 3 H). Step 2: 4-(((6-((trans-4-(tert-butyl)cyclohexyl)oxy)naphthalen-2-yl)methyl)amino)bicyclor2.2.21o ctane-l-carboxylic acid 2 M Lithium hydroxide, monohydrate in Water(2 mL, 4 mmol) was added to a solution of 4-{ [6-(trans-4-tert-Butyl-cyclohexyloxy)-naphthalen-2-ylmethyl]-amino}-bicyclo[2.2.2]o ctane-l-carboxylic acid methyl ester (217 mg, 0.454 mmol) in Tetrahydrofuran (2 mL, 20 mmol) and Methanol (1 mL, 20 mmol). The mixture was stirred at 70 C overnight. The solvent was concentrated. The residue was taken up in DMSO and TFA (200 mu,) was added to solubilize. Purification by preparative HPLC gave the product (135mg, 64%). HPLC (100%, RT=1.483 min), LCMS (100%, RT=1.64 min, m/z=464.30). 1H NMR (400 MHz, METHANOL-d4) delta ppm 0.94 (s, 9 H) 1.03 - 1.56 (m, 5 H) 1.94 (d, J=14.56 Hz, 2 H) 2.03 (d, J=7.03 Hz, 12 H) 2.29 (d, J=11.23 Hz, 2 H) 4.27 (s, 2 H) 4.33 - 4.46 (m, 1 H) 7.19 (d, J=11.36 Hz, 1 H) 7.30 (s, 1 H) 7.49 (d, J=8.41 Hz, 1 H) 7.82 (d, J=8.97 Hz, 1 H) 7.87 (d, J=8.60 Hz, 1 H) 7.90 (s, 1 H).

References: [1]Patent: WO2014/18891,2014,A1 .Location in patent: Page/Page column 150; 151.

24
[ 135908-33-7 ]
[ 1544655-87-9 ]

References: [1]Patent: WO2014/18891,2014,A1 .

25
[ 135908-33-7 ]
[ 1544656-10-1 ]

References: [1]Patent: WO2014/18891,2014,A1 .

26
[ 135908-33-7 ]
[ 1544656-15-6 ]

References: [1]Patent: WO2014/18891,2014,A1 .

27
[ 135908-33-7 ]
[ 1544656-39-4 ]

References: [1]Patent: WO2014/18891,2014,A1 .

28
[ 135908-33-7 ]
[ 1544656-65-6 ]

References: [1]Patent: WO2014/18891,2014,A1 .

29
[ 135908-33-7 ]
[ 1544661-90-6 ]

References: [1]Patent: WO2014/18891,2014,A1 .

30
[ 135908-33-7 ]
2-(cis-4-tert-butylcyclohexyloxy)-4-methyl-1-naphthaldehyde [ No CAS ]
[ 1621064-79-6 ]

Yield	Reaction Conditions	Operation in experiment
23%		Example 8 : 4- (((2- ((trans-4- (tert-butyl)c clohexyl)oxy) -4-methylnaphthalen- l-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylic acid To a mixture of 2-(cis-4-tert-butylcyclohexyloxy)-4-methyl-l-naphthaldehyde (lOOmg, 0.31 mmol, 1.0 eq) in toluene (1 mL) were added methyl 4- aminobicyclo[2.2.2]octane-l-carboxylate hydrochloride (81 mg, 0.37 mmol, 1.2 eq) and MgS04 (74 mg, 0.62 mmol, 2.0 eq). The resulting mixture was heated to reflux and stirred for 48 h. After being concentrated under reduced pressure, the residue was dissolved in THF (lmL). NaBH(OAc)3 (196 mg, 0.93 mmol, 3.0 eq) was added and the mixture was heated to reflux and stirred for 24 h. After cooling down to room temperature, the residue was diluted with EtOAc (5 mL). The suspension was filtered and the filtrate was concentrated under reduced pressure to give the residue, which was purified by column chromatography on silica gel (petroleum ether /EtOAc = 1/1) to yield the target ester (35 mg, 23 % yield) as a yellow oil. LCMS m/z 492.4 [M+H] +. Hydrolysis following standard condition gave the title compound as a white solid (20 mg, 69% yield). LCMS m/z 478.3 [M+H] +; 1H NMR (400 MHz, CD3OD) delta: 8.06- 8.01 (m, 2H), 7.61-7.59 (m, 1H), 7.49-7.47 (m, 1H), 7.36 (s, 1H), 4.54 (bs, 3H), 2.74 (s, 3H), 2.32-2.29 (m, 2H), 2.16 (bs, 12H), 1.99-1.94 (m, 2H), 1.54-1.51 (m, 2H), 1.34-1.24 (m, 2H), 1.20-1.14 (m, 1H), 0.91 (s, 9H).

References: [1]Patent: WO2014/120764,2014,A1 .Location in patent: Page/Page column 48-49.

31
[ 135908-33-7 ]
[ 1352066-57-9 ]
C₃₉H₅₀Cl₂N₂O₆S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10499 - 10511.

32
[ 135908-33-7 ]
[ 1352066-57-9 ]
4-(2-((3R,5R,6S)-1-((S)-2-(tert-butylsulfonyl)-1-cyclopropylethyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetamido)bicyclo[2.2.2]octane-1-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10499 - 10511.

33
[ 135908-33-7 ]
[ 1410737-09-5 ]
C₃₃H₃₆Cl₂FN₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
549 mg		HATU (616 mg, 1.62 mmol), DIEA (0.550 mL, 3.24 mmol) were added to a suspension of acid 1(500 mg, 1.08 mmol) in DCM (15 mL) and stuffed. After 10 minutes, methyl 4-aminobicyclo[2.2.2joctane-1-carboxylate (396 mg, 2.16 mmol) and DMAP (132 mg, 1.08 mmol) were added to the reaction. After overnight, the solvent was removed in vacuo and the crude was purified by column chromatography to give 549 mg of intermediate II.

References: [1]Patent: WO2015/161032,2015,A1 .Location in patent: Paragraph 0189.
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 2819 - 2839.

34
[ 135908-33-7 ]
4-((3'R,4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-1'-methyl-2''-oxodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indoline]-5'-carboxamido)bicyclo[2.2.2]octane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]

References: [1]Patent: WO2015/161032,2015,A1 .
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 2819 - 2839.

35
[ 135908-33-7 ]
C₃₃H₃₇Cl₂FN₄O₃*C₂HF₃O₂ [ No CAS ]

References: [1]Patent: WO2015/161032,2015,A1 .

36
[ 135908-33-7 ]
4-((3'R,4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-2''-oxodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indoline]-5'-carboxamido)bicyclo[2.2.2]octane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]

References: [1]Patent: WO2015/161032,2015,A1 .
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 2819 - 2839.

37
[ 135908-33-7 ]
(3'R,4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-N-(4-((methylsulfonyl)carbamoyl)bicyclo[2.2.2]octan-1-yl)-2''-oxodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indoline]-5'-carboxamide trifluoroacetic acid salt [ No CAS ]

References: [1]Patent: WO2015/161032,2015,A1 .
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 2819 - 2839.

38
[ 135908-33-7 ]
[ 79-22-1 ]
methyl 4-((methoxycarbonyl)amino)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; at 0 - 20℃;	Step A: Synthesis of methyl 4-((methoxycarbonyl)amino)bicyclo [2.2 .2loctane- 1 -carboxylateTo a solution of <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong> (260.4 mg, 1.42 1 mmol) wasadded K2C03 (589 mg, 4.26 mmol) in 5 ml water. Methyl carbonochloridate (0.143 ml, 1.847 mmol) was added at 0C and then the reaction was allowed to warm to RT and stirred overnight. Water was added and the crude product was extracted with DCM, dried over anhydrous Mg504, filtered, and concentrated to afford the desired compound. A small amount of DCM and hexanewas used to three or four times to precipitate the product. LCMS [M+1] = 242

References: [1]Patent: WO2015/164308,2015,A1 .Location in patent: Page/Page column 130.

39
[ 135908-33-7 ]
7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid [ No CAS ]
methyl 4-{7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-amido}bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62 mg		A mixture of 80 mg of 7 - [(2,6-difluorobenzyl) oxy] -2,5-dimethylpyrazolo [l, 5-a] pyridine-3-carboxylic acid (purity 75%, 0.181 mmol) from Example 4A, 76 mg of HATU (0.199 mmol) and 94 mu (0.542 mmol) Nu, Nu-diisopropylethylamine in 00:54 ml of DMF was stirred for 10 min at RT.Subsequently, 40 mg (0.217 mmol) of methyl 4-amino-bicyclo [2.2.2] octane-l-carboxylate was added and the mixture was stirred overnight at RT.The reaction mixture was mixed with water and acetonitrile and purified by preparative HPLC (RP18 column, eluent: acetonitrile / water gradient with addition of 0.05% formic acid).There were 62 mg of the target compound (70% d. Th.) Condition.

References: [1]Patent: TW2016/5850,2016,A .Location in patent: Paragraph 0385.

40
[ 135908-33-7 ]
4-[(pyrazolo[1,5-a]pyrimidin-3-ylcarbonyl)amino]bicyclo[2.2.2]octane-1-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/177658,2016,A1 .

41
[ 135908-33-7 ]
N-{4-[(2-chloro-4-fluorophenyl)carbamoyl]bicyclo[2.2.2]oct-1-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]

References: [1]Patent: WO2016/177658,2016,A1 .

42
[ 135908-33-7 ]
N-{4-[(2-chloro-4-fluoro-5-methylphenyl)carbamoyl]bicyclo[2.2.2]oct-1-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]

References: [1]Patent: WO2016/177658,2016,A1 .

43
[ 135908-33-7 ]
[ 59157-06-1 ]
[ 74-89-5 ]
methyl 4-([5-(methylcarbamoyl)-1H-imidazol-4-yl]carbonyl}amino)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
198 mg		Methyl 4-aminobicyclo[2.2.2]octane-1 -carboxylate (220 mg, 1 .20 mmol, Gas No 135908-33- 7) and N-ethyl-N-isopropylpropan-2-amine (0.31 ml, 1.8 mmol) were added to a suspensionof 5,1 0-dioxo-5H,1 OH-diimidazo[1 ,5-a:1 ,5-d]pyrazine-1 ,6-dicarbonyl dichloride (188 mg,0.600 mmol) in tetrahydrofuran (8.0 ml) and the mixture was stirred at room temperature.After 6 h, a solution of methanamine (0.60 ml, 1 .2 mmol, 2M solution in tetrahydrofuran) andN-ethyl-N-isopropylpropan-2-amine (0.31 ml, 1 .8 mmol) in tetrahydrofuran (8 ml) was addedand the mixture was stirred over night at room temperature. For work-up, precipitates werefiltered off and washed with tetrahydrofuran. The combined filtrates were concentrated andpurified by flash chromatography (Snap Gartridge, hexanes/ethyl acetate gradient 50 % -> 100% ethyl acetate) to provide the title compound (198 mg).LG-MS (Method 2): R = 0.89 mm; MS (ESIpos) m/z = 335.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 13.32-12.85 (m, 1H), 11.42-10.51 (m, 1H), 8.93-8.16 (m, 1H), 7.74 (5, 1H), 3.57 (5, 3H), 2.78 (d, 3H), 2.06-1.90 (m, 6H), 1.89-1.70 (m, 6H).

References: [1]Patent: WO2016/177658,2016,A1 .Location in patent: Page/Page column 216.

44
[ 135908-33-7 ]
[ 25940-35-6 ]
methyl 4-[(pyrazolo[1,5-a]pyrimidin-3-ylcarbonyl)amino]bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
453 mg	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	(Benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (687 mg, 1 .32 mmol) was added to a mixture of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (196 mg, 1.20 mmol, CAS No. 25940-35-6), <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong> (242 mg, 1.32 mmol, Cas No 135908-33-7) and N-ethyl-N-isopropylpropan-2-amine (0.84 ml, 4.80 mmol) inN,N-dimethylformamide (13 ml) and the mixture was stirred over night at room temperature. For work-up the reaction mixuture was concentrated under reduced pressure and the residue was purified by flash chromatogryph (Snap Cartridge, hexanes/ethyl acetate gradient 0% ->100% ethyl acetate) to yield methyl 4-[(pyrazolo[1 ,5-a]pyrimidin-3-ylcarbonyl)amino]bicyclo[2.2.2]octane-1 -carboxylate (453 mg, 115% yield).[C-MS (Method 2): R = 0.97 mm; MS (ESIpos) m/z = 329.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.31 (dd, 1H), 8.79 (dd, 1H), 8.52 (5, 1H), 7.69 (5,1 H), 7.26 (dd, 1 H), 3.59 (5, 3H), 2.08-1.94 (m, 6H), 1.92-1.77 (m, 6H).

References: [1]Patent: WO2016/177658,2016,A1 .Location in patent: Page/Page column 217; 218.

45
[ 135908-33-7 ]
4-((3'R,4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-1'-ethyl-2''-oxodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indoline]-5'-carboxamido)bicyclo[2.2.2]octane-1-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 2819 - 2839.

46
[ 135908-33-7 ]
C₂₃H₁₉Cl₂F₃N₂O₃ [ No CAS ]
C₃₃H₃₄Cl₂F₃N₃O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 2819 - 2839.

47
[ 135908-33-7 ]
6-chloro-3-methyl-2-phenylquinoline-4-carboxylic acid [ No CAS ]
methyl 4-[(6-chloro-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60℃; for 1h;	At RT, 258 mg (1.41 mmol) of <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong>, 402 mg (1.06 mmol) of HATU and 182 mg (1.41 mmol) of DIPEA were added to a solution of 210 mg (0.71 mmol) of 6-chloro-3-methyl-2-phenylquinoline-4-carboxylic acid in 5 ml of DMF. The mixture was then stirred at 60 C. for 1 h. After cooling to RT, the mixture was added to 20 ml of a 10% strength citric acid solution. The resulting precipitate was filtered off, washed with water and dried under reduced to pressure. This gave 326 mg (97% of theory, purity 98%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.48 (s, 1H), 8.05 (d, 1H), 7.77 (dd, 1H), 7.66 (d, 1H), 7.60-7.47 (m, 5H), 3.59 (s, 3H), 2.32 (s, 3H), 2.09-2.00 (m, 6H), 1.91-1.82 (m, 6H). LC/MS (Method 1, ESIpos): Rt=1.22 min, m/z=463 [M+H]+.

References: [1]Patent: US2018/36300,2018,A1 .Location in patent: Paragraph 0534-0537.

48
[ 135908-33-7 ]
6-bromo-3-cyclopropyl-2-phenylquinoline-4-carboxylic acid [ No CAS ]
methyl 4-[(6-bromo-3-cyclopropyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60℃; for 27h;	At RT, 119 mg (0.54 mmol) of <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong>, 310 mg (0.82 mmol) of HATU and 0.28 ml (1.63 mmol) of DIPEA were added to a solution of 200 mg (0.54 mmol) of the compound from Example 36A in 3 ml of DMF, and the mixture was stirred at 60 C. for 5 h. Subsequently, a further 0.19 ml (1.11 mmol) of DIPEA were added, and the mixture was stirred at 60 C. for a further 22 h. After cooling to RT, the mixture was introduced into 50 ml of 10% strength citric acid solution and extracted twice with in each case 30 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated and the residue was taken up in a little DMSO and acetonitrile and purified by preparative HPLC (Method 3). This gave 84 mg (29% of theory, purity 100%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.41 (s, 1H), 7.97 (d, 1H), 7.92 (d, 1H), 7.88 (dd, 1H), 7.72-7.66 (m, 2H), 7.54-7.42 (min, 3H), 3.60 (s, 3H), 2.30-2.17 (min, 1H), 2.13-2.00 (min, 6H), 1.93-1.79 (m, 6H), 0.72-0.58 (m, 2H), 0.38-0.22 (m, 2H). LC/MS (Method 1, ESIpos): Rt=1.27 min, m/z=533/535 [M+H]+.

References: [1]Patent: US2018/36300,2018,A1 .Location in patent: Paragraph 0633-0637.

49
[ 135908-33-7 ]
6-chloro-3-methyl-2-phenylquinoline-4-carboxylic acid [ No CAS ]
4-[(6-chloro-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylic acid [ No CAS ]

References: [1]Patent: US2018/36300,2018,A1 .

50
[ 135908-33-7 ]
6-bromo-3-methyl-2-phenylquinoline-4-carboxylic acid [ No CAS ]
methyl 4-[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60℃;	At RT, 214 mg (1.17 mmol) of <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong>, 333 mg (0.88 mmol) of HATU and 0.20 ml (1.17 mmol) of DIPEA were added successively to a solution of 200 mg (0.58 mmol) of the compound from Example 3A in 3 ml of DMF. The mixture was then stirred at 60 C. overnight. After cooling to RT, the mixture was purified directly (without further work-up) by preparative HPLC (Method 2). This gave 269 mg (90% of theory, purity 99%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.48 (s, 1H), 7.97 (d, 1H), 7.88 (dd, 1H), 7.83 (d, 1H), 7.65-7.42 (min, 5H), 3.59 (s, 3H), 2.32 (s, 3H), 2.12-1.95 (min, 6H), 1.94-1.76 (min, 6H). LC/MS (Method 1, ESIpos): Rt=1.20 min, m/z=507/509 [M+H]+.

References: [1]Patent: US2018/36300,2018,A1 .Location in patent: Paragraph 0530-0533.

51
[ 135908-33-7 ]
6-tert-butyl-3-methyl-2-phenylquinoline-4-carboxylic acid [ No CAS ]
methyl 4-[(6-tert-butyl-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60℃;	At RT, 241 mg (1.32 mmol) of <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong>, 375 mg (0.99 mmol) of HATU and 0.23 ml (1.32 mmol) of DIPEA were added successively to a solution of 210 mg (0.66 mmol) of the compound from Example 5A in 5 ml of DMF. The mixture was then stirred at 60 C. overnight. After cooling to RT, the mixture was added with stirring to 20 ml of a 10% strength citric acid solution. The resulting solid was then filtered off, washed three times with water and once with pentane and then dried under reduced pressure. This gave 314 mg (93% of theory, purity 95%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.46 (s, 1H), 7.98 (d, 1H), 7.93 (d, 1H), 7.70 (d, 1H), 7.60-7.46 (m, 5H), 3.59 (s, 3H), 2.31 (s, 3H), 2.10-2.00 (m, 6H), 1.91-1.82 (m, 6H), 1.38 (s, 9H). LC/MS (Method 1, ESIpos): Rt=1.22 min, m/z=485 [M+H]+.

References: [1]Patent: US2018/36300,2018,A1 .Location in patent: Paragraph 0542-0545.

52
[ 135908-33-7 ]
6-bromo-3-fluoro-2-phenylquinoline-4-carboxylic acid [ No CAS ]
C₂₆H₂₄BrFN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60℃; for 1h;	At RT, 159 mg (0.87 mmol) of <strong>[135908-33-7]methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate</strong>, 247 mg (0.65 mmol) of HATU and 112 mg (0.87 mmol) of DIPEA were added to a solution of 150 mg (0.43 mmol) of the compound from Example 12A in 4 ml of DMF, and the mixture was then stirred at 60 C. for 1 h. After cooling to RT, the mixture was added to 20 ml of a 10% strength citric acid solution. The resulting precipitate was then filtered off, washed with water and dried under reduced pressure. This gave 222 mg (97% of theory, purity 97%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.65 (s, 1H), 8.08 (d, 1H), 8.04-7.97 (m, 2H), 7.95 (dd, 1H), 7.91 (d, 1H), 7.63-7.53 (m, 3H), 3.59 (s, 3H), 2.08-1.98 (m, 6H), 1.91-1.82 (m, 6H). LC/MS (Method 1, ESIpos): Rt=1.26 min, m/z=511/513 [M+H]+.

References: [1]Patent: US2018/36300,2018,A1 .Location in patent: Paragraph 0573-0576.

53
[ 135908-33-7 ]
(trans)-3-(benzo[d]thiazol-4-yloxy)cyclobutanecarboxylic acid [ No CAS ]
methyl 4-((trans)-3-(benzo[d]thiazol-4-yloxy)cyclobutane-1-carboxamido)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	To a stirred, cooled (0 C) solution of (trans)-3-(benzo[d]thiazol-4- yloxy)cyclobutane-1 -carboxylic acid (100 mg, 0.401 mmol, Intermediate 25) and methyl 4- aminobicyclo[2.2.2]octane-1 -carboxylate (75 mg, 0.409 mmol) in N,N-dimethylformamide (2 mL) was added N,N-diisopropylethylamine (0.25 mL, 1 .431 mmol), followed by a 50% solution of 2,4,6-tripropyl-1 ,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) in ethyl acetate (0.75 mL, 1 .260 mmol). The mixture was allowed to warm slowly to room temperature, while stirring for 2 hours, quenched with saturated aqueous sodium bicarbonate, and extracted with dichloromethane (2X). The combined organic layers were washed with brine, dried over sodium sulfate, and filtered. Solvent was removed under reduced pressure. The remaining material was dissolved in a minimal amount of dichloromethane and chromatographed on silica gel, eluting with a 5%-70% ethyl acetate:ethanol (3:1 v/v) in hexanes gradient to give the title compound (120 mg, 72%) as a white solid. 1H NMR (400 MHz, CD3SOCD3) delta 1 .73-1 .89 (m, 12 H), 2.27-2.35 (m, 2 H), 2.54-2.61 (m, 2 H), 3.07 (tt, J = 9., 5 Hz, 1 H), 3.57 (s, 3 H), 5.03 (quin, J = 6 Hz, 1 H), 6.81 (d, J = 8 Hz, 1 H), 7.38 (t, J = 8 Hz, 1 H), 7.43 (s, 1 H), 7.69 (d, J = 8 Hz, 1 H), 9.25 (s, 1 H); LC-MS (LC-ES) M+H = 415.

References: [1]Patent: WO2018/69863,2018,A1 .Location in patent: Page/Page column 481.

54
[ 135908-33-7 ]
4-(azetidin-3-yloxy)benzo[d]thiazole hydrochloride [ No CAS ]
[ 7693-46-1 ]
methyl 4-(3-(benzo[d]thiazol-4-yloxy)azetidine-1-carboxamido)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		To a stirred, cooled (0 C) solution of 4-nitrophenyl chloroformate (1 15 mg, 0.571 mmol) and methyl 4-aminobicyclo[2.2.2]octane-1 -carboxylate (100 mg, 0.546 mmol) in dichloromethane (3 mL) was added pyridine (1 .20 mL, 14.8 mmol). The mixture was stirred for 2 hours and then 4-(azetidin-3-yloxy)benzo[d]thiazole hydrochloride (120 mg, 0.494 mmol, Intermediate 28) was added, followed by N,N-diisopropylethylamine (0.30 mL, 1 .72 mmol). After stirring overnight, the mixture was poured into 1 N aqueous sodium hydroxide and extracted with dichloromethane (2X). The combined organic layers were washed with brine, dried over sodium sulfate, and filtered. Solvent was removed under reduced pressure. The remaining material was dissolved in a minimal amount of dichloromethane and chromatographed on silica gel, eluting with a 5%-50% ethyl acetate:ethanol (3:1 v/v) in hexanes gradient to give the title compound (95 mg, 46%) as a white solid. 1H NMR (400 MHz, CD3SOCD3) delta 1 .78 (q, J = 9 Hz, 12 H), 3.56 (s, 3 H), 3.82 (dd, J = 9, 4 Hz, 2 H), 4.27 (dd, J = 9, 6 Hz, 2 H), 5.18 (td, J = 7, 3 Hz, 1 H), 5.80 (s, 1 H), 6.84 (d, J = 8 Hz, 1 H), 7.40 (t, J = 8 Hz, 1 H), 7.73-7.77 (m, 1 H), 9.30 (s, 1 H); LC-MS (LC-ES) M+H = 416.

References: [1]Patent: WO2018/69863,2018,A1 .Location in patent: Page/Page column 482.

55
[ 135908-33-7 ]
[ 108-23-6 ]
methyl 4-(isopropoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane;	General method D, 4-(isopropoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate.

References: [1]Patent: US2019/77799,2019,A1 .Location in patent: Paragraph 0312-0313.

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 • 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-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 135908-33-7 ]

Aliphatic Cyclic Hydrocarbons

A124133 [135908-43-9]

Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride

Similarity: 0.97

A112644 [62456-15-9]

trans-Methyl 4-aminocyclohexanecarboxylate

Similarity: 0.94

A130697 [1401333-04-7]

(Z)-Methyl 4-aminoadamantane-1-carboxylate hydrochloride

Similarity: 0.92

A109857 [61367-07-5]

Methyl trans-4-aminocyclohexanecarboxylate hydrochloride

Similarity: 0.92

A189593 [61367-16-6]

cis-Methyl 4-aminocyclohexanecarboxylate hydrochloride

Similarity: 0.92

Esters

A124133 [135908-43-9]

Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride

Similarity: 0.97

A112644 [62456-15-9]

trans-Methyl 4-aminocyclohexanecarboxylate

Similarity: 0.94

A130697 [1401333-04-7]

(Z)-Methyl 4-aminoadamantane-1-carboxylate hydrochloride

Similarity: 0.92

A109857 [61367-07-5]

Methyl trans-4-aminocyclohexanecarboxylate hydrochloride

Similarity: 0.92

A189593 [61367-16-6]

cis-Methyl 4-aminocyclohexanecarboxylate hydrochloride

Similarity: 0.92

Amines

A124133 [135908-43-9]

Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride

Similarity: 0.97

A112644 [62456-15-9]

trans-Methyl 4-aminocyclohexanecarboxylate

Similarity: 0.94

A130697 [1401333-04-7]

(Z)-Methyl 4-aminoadamantane-1-carboxylate hydrochloride

Similarity: 0.92

A109857 [61367-07-5]

Methyl trans-4-aminocyclohexanecarboxylate hydrochloride

Similarity: 0.92

A189593 [61367-16-6]

cis-Methyl 4-aminocyclohexanecarboxylate hydrochloride

Similarity: 0.92

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CAS No.: 135908-33-7

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CAS No.: 135908-33-7

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CAS No.: 135908-33-7

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[ 135908-33-7 ] Synthesis Path-Downstream 1~55

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