[ CAS No. 22287-28-1 ] {[proInfo.proName]}

Name: 22287-28-1|Bicyclo[1.1.1]pentane-1-carboxylic acid|98%
Brand: Ambeed
SKU: A103228
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Product Details of [ 22287-28-1 ]

CAS No. :	22287-28-1	MDL No. :	MFCD19228106
Formula :	C₆H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ORCXPYPDHLVQFP-UHFFFAOYSA-N
M.W :	112.13	Pubchem ID :	11297945
Synonyms :

Safety of [ 22287-28-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22287-28-1 ]

* 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.

Upstream synthesis route of [ 22287-28-1 ]
Downstream synthetic route of [ 22287-28-1 ]

[ 22287-28-1 ] Synthesis Path-Upstream 1~1

1
[ 22287-28-1 ]
[ 22287-35-0 ]

Reference： [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 43, p. 6450 - 6456

[ 22287-28-1 ] Synthesis Path-Downstream 1~20

1
[ 106813-54-1 ]
[ 22287-28-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In ethanol Heating; Yield given;

Reference： [1]Kaszynski, Piotr; Friedli, Andrienne C.; Michl, Josef [Journal of the American Chemical Society, 1992, vol. 114, # 2, p. 601 - 620]

2
[ 22287-28-1 ]
[ 22287-32-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 24℃; for 16h;	To a solution of <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (4.0 g, 35.7 mmol) in tetrahydrofuran (89 mL) at 0 C. was added lithium aluminum hydride (1.801 g, 47.4 mmol) in portions and the reaction bubbled vigorously. The reaction was warmed to 24 C. and was stirred for 16 hours. The reaction was cooled in an ice bath and 4 g of sodium sulfate decahydrate was added in portions and the reaction was stirred for 1 hour. Aqueous NaOH solution (15%, 2 mL) was added, the reaction mixture was stirred for 0.5 hours, water (2 mL) was added, the ice-bath was removed and the mixture was stirred for 2 hours. The mixture was dried with 40 g anhydrous sodium sulfate. The suspension was filtered and the filtrate was washed with ether. The solvent was removed in vacuo to provide crude bicyclo[1.1.1]pentan-1-ylmethanol (3.2 g, 32.6 mmol, 91% yield). 1H NMR (501 MHz, Chloroform-d) δ ppm 3.56 (s, 2H), 2.57 (s, 1H), 1.77 (s, 6H).
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1h;	To a solution of <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (250 mg, 2.230 mmol) in THF (1 mL) was added LiAlH4 (127 mg, 3.34 mmol) at 0 C. The reaction was allowed to warm to RT and was stirred for 1 h before quenching with water (0.25 mL) and anhydrous Na2SO4 (1 g). After stirring for 20 min, the mixture was filtered and washed with THF. The crude solution was used directly in the next step without further purification.
80 mg	With lithium aluminium tetrahydride; In diethyl ether; for 2h;Reflux; Inert atmosphere;	Compound 1-7 (120 mg, 1.10 mmol) was dissolved in diethyl ether (20 mL) in a 50 mL single-necked flask, Lithium aluminum tetrahydrate (53 mg, 1.5 mmol) was added under reflux with ice, and the reaction 2h was refluxed. (0.05 mL), 15% aqueous sodium hydroxide solution (0.05 mL) and water (0.15 mL) were added dropwise under ice-cooling, filtered and the filtrate was concentrated to give 80 mg of product as a pale yellow oil

With lithium aluminium tetrahydride; In diethyl ether; at 50℃; for 2h;Inert atmosphere;

To a mixture of LAH (271 mg, 7.13 mmol) in Et2O (4 mL) was added a solution of (0281) <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (400 mg, 3.57 mmol) in Et2O (1 mL) under N2 at 50C. The mixture was stirred at 50C for 2 h. TLC showed the reaction was complete. The reaction mixture was diluted with DCM (10 mL) and water (0.5 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuum to give the crude title compound, which was used directly in the next step.

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1329 - 1333
[2]Patent: US2018/99931,2018,A1 .Location in patent: Paragraph 2159; 2355
[3]Patent: US2017/183342,2017,A1 .Location in patent: Paragraph 0317
[4]Patent: CN107200734,2017,A .Location in patent: Paragraph 0114-0115; 0126-0127
[5]Patent: WO2018/39094,2018,A1 .Location in patent: Page/Page column 40

3
[ 22287-28-1 ]
[ 22287-34-9 ]

Yield	Reaction Conditions	Operation in experiment
99.9%	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃;	To a stirred solution of bicyclo[ 1.1.1 ]pentane-l-carboxylic acid (3.86 g, 34.4 mmol) in dry DCM (60 ml), was added drop of DMF followed dropwise addition of oxalyl chloride (5.03 g, 39.6 mmol). The reaction mixture was stirred at r.t. until gas release was complete. The mixture was concentrated and bicyclo[l.l.l]pentane-l-carbonyl chloride (4.49 g, 34.4 mmol, 99.9% yield) was used in the next step without further purification.

Reference： [1]Patent: WO2019/86142,2019,A1 .Location in patent: Page/Page column 105
[2]Australian Journal of Chemistry,1989,vol. 42,p. 61 - 69
[3]Journal of the American Chemical Society,1987,vol. 109,p. 2746
[4]Tetrahedron Letters,1996,vol. 37,p. 8059 - 8060

4
[ 22287-28-1 ]
[ 107474-98-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 98A bicyclo[1.1.1]pentane-1-carboxamide To a mixture of <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (4 g) in dichloromethane (40 mL) was added thionyl chloride (4.7 mL). The reaction mixture was heated to reflux for 18 hours. The mixture was cooled to 0 C. and was added to aqueous ammonium hydroxide (9 mL) at 0 C. for 30 minutes. The resulting mixture was filtered to provide the title compound which was used in the next step without further purification. 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ ppm 7.16 (br s, 1H), 6.85 (br s, 1H), 2.37-2.32 (m, 1H), 1.89 (s, 6H).

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 2746
[2]Patent: US2019/55264,2019,A1 .Location in patent: Paragraph 0971

5
[ 22287-28-1 ]
[ 128884-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 1.5 h / 5 °C 2: 90 percent / 2-bromo-2-chloro-1,1,1-trifluoroethane, 4-dimethylaminopyridine / 1 h / Heating; Irradiation

Reference： [1]Della, Ernest W.; Taylor, Dennis K. [Australian Journal of Chemistry, 1990, vol. 43, # 5, p. 945 - 948]

6
[ 22287-28-1 ]
1-((1H-indol-3-yl)methyl)cyclopropane-1-amine [ No CAS ]
N-(1-((1H-indol-3-yl)methyl)cyclopropyl)bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		To a stirred solution of 1-((1H-indol-3- yl)methyl)cyclopropanamine (0.19 g, 1.02 mmol) in DCM (3.92 ml) were added HATU (0.312 g, 1.33 mmol) and N,N-diisopropylethylamine (0.355 ml, 2.04 mmol) at rt. The mixture was stirred for 10 mm and <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (0.126 g, 1.12 mmol) was added. After being stirred at rt for 16 h, the mixture was diluted with ethyl acetate (15 mL) and washed with saturated aqueous NaHCO3 solution. The organic layer was separated, dried over Na2504, filtered and concentrated. The resulting residue was purified by flash chromatography (5i02, 30-60% EtOAc in hexane) to afford N-(1-((1H-indol-3- yl)methyl)cyclopropyl)bicyclo[ 1.1.1 ]pentane- 1 -carboxamide (0.20 g, 0.713 mmol, 70% yield) as an off-white solid. MS (APCI) m/z 281.16 [M+H].

Reference： [1]Patent: WO2017/172957,2017,A1 .Location in patent: Paragraph 0263

7
[ 304-53-0 ]
[ 22287-28-1 ]
N-(1-(1H-indol-3-yl)-2-methylpropan-2-yl)bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		To a stirred solution of 1-(1H-indol-3-yl)-2-methylpropan-2-amine (0.31 g, 1.65 mmol) in DCM (6.33 ml) were added HATU (0.504 g, 2.14 mmol) and N,N-diisopropylethylamine (0.574 ml, 3.29 mmol) at rt. The mixture was stirred for 10 mm at rt and <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (0.203 g, 1.81 mmol) was added. After being stirred at rt for 16 h, the reaction mixture was diluted with EtOAc (15 mL) and washed with saturated aqueous NaHCO3 solution. The organic layer was separated, dried over Na2504, filtered and concentrated. The resulting residue was purified by flash chromatography (5i02, 30-60% EtOAc in hexane) to afford N-(1-(1H-indol-3-yl)-2- methylpropan-2-yl)bicyclo[ 1.1.1 ]pentane- 1 -carboxamide (0.36 g, 77% yield). MS (APCI) m/z 283.17 [M+H].

Reference： [1]Patent: WO2017/172957,2017,A1 .Location in patent: Paragraph 0249

8
[ 22287-28-1 ]
[ 7795-52-0 ]
(R)-N-(1-(1H-indol-3-yl)propan-2-yl)bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		To a stirred solution of (R)-1-(1H-indol-3-yl)propan-2-amine (0.500 g, 2.87 mmol) in THF (10 mL) was added propylphosphonic anhydride (2.25 mL, 8.60 mmol, 50% wt/wt in EtOAc) and N,N-diisopropylethylamine (1.5 mL, 8.60 mmol) at rt. The solution was stirred for 10 minutes and then a solution of <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (0.375 g, 3.16 mmol) was added and the mixture was stirred at rt for an additional 16 h. Water (3 mL) was added and the reaction mixture was extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over Na2504, filtered and evaporated under reduced pressure. The crude product was triturated with ether to obtain 700 mg (90% yield) of (R)-N(1 -( 1H-indol-3 -yl)propan-2-yl)bicyclo[ 1.1.1 ]pentane- 1 -carboxamide of the formula as a pale yellow solid. MS (ESI) m/z 269.26 [M+H].

Reference： [1]Patent: WO2017/172957,2017,A1 .Location in patent: Paragraph 0161

9
[ 524-38-9 ]
[ 22287-28-1 ]
1,3-dioxoisoindolin-2-yl bicyclo[1.1.1]pentane-1-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2020
[2]Science,2017,vol. 357,p. 283 - 286

10
[ 22287-28-1 ]
[ 22287-35-0 ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6450 - 6456

11
[ 22287-28-1 ]
[ 117633-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 24 °C 2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.5 h / -65 °C 2.2: 0.17 h / -78 °C

Reference： [1]Current Patent Assignee: ABBVIE INC; GALAPAGOS - US2018/99931, 2018, A1

12
[ 22287-28-1 ]
3-methyl-6-oxo-8-(pyridin-3-yl)-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile [ No CAS ]
8-(6-(bicyclo[1.1.1]pentan-1-yl)pyridin-3-yl)-3-methyl-6-oxo-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile [ No CAS ]
8-(2-(bicyclo[1.1.1]pentan-1-yl)pyridin-3-yl)-3-methyl-6-oxo-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile [ No CAS ]
8-(2,6-di(bicyclo[1.1.1]pentan-1-yl)pyridin-3-yl)-3-methyl-6-oxo-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.3%; 5.7%; 3.7%	With ammonium persulfate; silver nitrate; In water; acetonitrile; at 0 - 45℃; for 16.5h;Sealed tube;	[00434] To a stirred suspension of 3-methyl-6-oxo-8-(pyridin-3-yl)-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile (1 , 0.15 g, 0.53 mmol), bicyclo[1.1.1]pentane-1- carboxylic acid (0.05 g, 0.44 mmol) and silver nitrate (0.09 g, 0.53 mmol) in acetonitrile:water mixture (5 mL, 1 :1 ), was added a solution of ammonium persulfate (0.20 g, 0.89 mmol) in acetonitrile:water mixture (5 mL, 1 :1 ) drop wise over 10 min at 0 C. The resulting mixture was brought to room temperature over 30 min (reaction mixture changed into clear solution). Then the reaction mixture was stirred at 45 C for 16 h in a sealed tube. The reaction mixture was basified to pH 9 with saturated sodium bicarbonate solution and extracted with ethyl acetate (20 mL x 2). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified by silica gel column chromatography to afford the title compounds 8-(6-(bicyclo[1.1.1]pentan-1-yl)pyridin-3-yl)-3-methyl-6-oxo-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile (2 (example 148), 0.01 g, 6.3% yield) as a white solid, 8-(2-(bicyclo[1.1.1]pentan-1-yl)pyridin-3-yl)-3-methyl-6-oxo-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile (3 (example 149), 0.09 g, 5.7% yield) as a white solid and 8-(2,6-di(bicyclo[1.1.1]pentan-1-yl)pyridin-3-yl)-3-methyl-6-oxo-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile (4 (example 150), 0.07 g , 3.7% yield) as a white solid.

Reference： [1]Patent: WO2018/119374,2018,A1 .Location in patent: Paragraph 00430-00435

13
[ 22287-28-1 ]
tert-butyl-[[2-[(2-fluorophenyl)methyl]-7-methoxy-spiro[3,9-dihydro-1H-pyrido[3,4-b]indole-4,4’-piperidine]-1-yl]methoxy]-dimethyl-silane [ No CAS ]
1-bicyclo[1.1.1]pentanyl-[2-[(2-fluorophenyl)methyl]-1-(hydroxymethyl)-7-methoxy-spiro[3,9-dihydro-1H-pyrido[3,4-b]indole-4,4‘-piperidine]-1‘-yl]methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45 mg		To a solution of tert-butyl-[[2-[(2-fluorophenyl)methyl]-7-methoxy-spiro[3,9-dihydro-1 H- pyrido[3,4-b]indole-4,4’-piperidine]-l-yl]methoxy]-dimethyl-silane (100 mg, 191 umol) and bicyclo[1.1.1]pentane-1- carboxylic acid (25.69 mg, 229.11 imol) in DCM (10 mL) was added DIPEA (74 mg, 572.79 jimol, 100 iL) and HATU (145.2 mg, 381.8 imol). The mixturewas stirred at25 Cfor 16 hours. The reactionmixture was poured into H20 (200 mL) and extracted with ethyl acetate (20 mL3). The combined organic layer was washed with H20 (20 mL3) and brine (10 mL2), dried over Na2SO4, and concentrated undervacuum. The residue was dissolved in THE (20 mL) and TBAF (1 M, 1.12 mL)was added. The mixturewas stirred at 30 C for 3 hours. The reaction mixture was diluted with ethyl acetate (1 00 mL) and washed with H20 (20 mL6), then dried over anhydrous Na2SO4 and concentrated under vacuum. The residuewas purified by Pre-HPLC (column: Phenomenex Synergi 018 15025lOjlm; mobile phase:[water(0.1 %TFA) -ACN];B%: 1 8%-48%,1 2mm). 1 -bicyclo[1 .1 .1]pentanyl-[2-[(2-fluorophenyl) methyl]-1 -(hydroxymethyl)-7-methoxy-spiro[3,9-dihydro-1 H-pyrido[3,4-b]indole-4,4’-piperidine]-l ‘-yl]methanone (45mg) as a light yellow solid).1H NMR (400 MHz, METHANOL-d4) 61.70-1.95 (m, 2H), 2.19-2.30 (m, 6H), 2.30-2.55 (m, SH), 2.64-2.75(m, 1 H), 3.11 -3.22(m, 1 H), 3.60-3.64 (m, 1 H), 3.82 (s, 3H), 4.00-4.05 (m, 1 H), 4.21-4.37 (m, 3H), 4.41-4.46 (m, 1H), 4.63-4.84 (m, 3H), 6.72-6.76(m, 1H), 6.93(d, J2.26 Hz, 1H), 7.31 -7.45 (m, 3H), 7.61 (q,J=6.57 Hz, 1H),7.68-7.78 (m, 1H); LCMS (ESI) m/z: [M+H] = 504.5 (Method: 5-95ABR210&254).

Reference： [1]Patent: WO2018/213422,2018,A1 .Location in patent: Page/Page column 116; 117

14
[ 218594-15-1 ]
[ 22287-28-1 ]
tert-butyl (6-(bicyclo[1.1.1]pentan-1-yl)pyridin-3-yl)carbamate [ No CAS ]

Reference： [1]Organic Letters,2020

15
[ 22287-28-1 ]
(S)-(3-aminoazetidin-1-yl)(5-((1-(5-fluoropyridin-3-yl)ethyl)amino)-2-methylthiazolo[4,5-d]pyrimidin-7-yl)methanone trihydrochloride [ No CAS ]
(S)-N-(1-(5-((1-(5-fluoropyridin-3-yl)ethyl)amino)-2-methylthiazolo[4,5-d]pyrimidine-7-carbonyl)azetidin-3-yl)bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	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 20℃; for 2h;	Synthesis of (S)-N-(1-(5-((1-(5-fluoropyridin-3-yl)ethyl)amino)-2-methylthiazolo[4,5-d]pyrimidine-7-carbonyl)azetidin-3-yl)bicyclo[1.1.1]pentane-1-carboxamide (66): To a solution of (S)-(3-aminoazetidin-1-yl)(5-((1-(5-fluoropyridin-3-yl)ethyl)amino)-2-methylthiazolo[4,5-d]pyrimidin-7-yl)methanone (9.7 mg, 0.025 mmol) in DMF (1 mL) were added bicyclo[1.1.1]pentane-3-carboxylic acid (4.2 mg, 0.0375 mmol) (commercially available from PharmaBlock, Nanjing, China), HATU (14 mg, 0.0375 mmol), and DIEA (13 uL, 0.0725 mmol). The mixture thus obtained was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate and washed with 5% NaHCO3, water, and brine, then dried over MgSO4. The solvent was evaporated in vacuo and the residue was purified flash chromatography on silica gel (4 g HP silica, Teledyne Isco) eluting with 10% to 50% solvent A (DCM/MeOH/NH4OH, 100/10/1) in DCM to provide 66 as a white solid (11 mg, 91% yield). 1H NMR (400 MHz, DMSO-d6 at 80 C) δ 1.57 (3H, d, J = 6.8 Hz), 1.99 (6H, d, J = 1.6 Hz), 2.43 (1H, br s), 2.78 (3H, s), 4.02 (1H, m), 4.33 (1H, m), 4.47 (1H, m), 4.58 (1H, m), 4.93 (1H, m), 5.25 (1H, quintet, J = 6.8 Hz), 7.70 (1H, m), 7.84 (1H, d, J = 8.0 Hz), 8.12 (1H, m), 8.39 (1H, d, J = 2.8 Hz), 8.52 (1H, d, J = 8.0 Hz) ppm. ESI MS: m/z [M+H+] for C23H24FN7O2S, calcd 482.1, found 482.1.

Reference： [1]Patent: EP3616753,2020,A1 .Location in patent: Paragraph 0813-0814

16
[ 22287-28-1 ]
[ 74903-79-0 ]
(Z)-N-((bicyclo[1.1.1]pentane-1-carbonyl)oxy)-4-methoxybenzimidoyl chloride [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 21875 - 21879
Angew. Chem.,2020,vol. 132,p. 22059 - 22063,5

17
[ 936-47-0 ]
[ 22287-28-1 ]
C₈H₅F₂NO [ No CAS ]
Bicyclo[1.1.1]pentan-1-yl(5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%		To a stirring solution of <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (17 mg, 0.15 mmol) in DMF (0.5 ml) was added iPr2NEt (0.048 ml, 0.27 mmol), then in 10 min HATU (78 mg, 0.205 mmol), then in 15 min 5-phenyl-4,5-dihydro-1H-pyrazole (20 mg, 0.137 mmol). The reaction was stirred for 2 h at RT. Saturated NaHCO3 was then added, and the layers were separated. The aqueous phase was extracted with EtOAc (3*) and the combined organic layers were concentrated under reduced pressure. The residue was purified by mass-triggered preparative HPLC (Mobile phase: A=0.1% TFA/H2O, B=0.1% TFA/MeCN; Gradient: B=30-70%; 20 min; Column: C18) to give the title compound (7 mg, 0.027 mmol, 20% yield) as a yellow amorphous material. MS (ES+) C15H16N2O requires: 240, found: 241 [M+H]+.

Reference： [1]Patent: US2021/94921,2021,A1 .Location in patent: Paragraph 0788-0790

18
[ 22287-28-1 ]
[ 98021-39-7 ]
N'-[bicyclo[1.1.1]pentane-1-carbonyl]-6-oxo-1H-pyridazine-3-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.90%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 4h;	[0291] To a stirred solution of 6-oxo-1H-pyridazine-3-carbohydrazide (500.00 mg, 3.24 mmol) in DMF (8.00 mL) were added <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (363.30 mg, 3.24 mmol), PyBOP (2.19 g, 4.21 mmol) and DIPEA (1.26 g, 9.72 mmol). The reaction mixture was stirred for 4 h at room temperature. The reaction was diluted by the addition of H2O (12.0 mL). The precipitated solids were collected by filtration and washed with ACN (2x2 mL) to give the title compound as a white solid (450 mg, 48.90%) MS m/z: 249 [M+H]+.

Reference： [1]Patent: WO2021/231565,2021,A1 .Location in patent: Paragraph 0291

19
[ 22287-28-1 ]
N-(6-ethyl-1,3-benzothiazol-2-yl)-N-[(pyridin-3-yl)methyl]piperidine-4-carboxamide [ No CAS ]
1-{bicyclo[1.1.1]pentane-1-carbonyl}-N-(6-ethyl-1,3-benzothiazol-2-yl)-N-[(pyridin-3-yl)methyl]piperidine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 16h;	A solution of N-(6-ethylbenzo[d]thiazol-2-yl)-N-(pyridin-3-ylmethyl)piperidine-4-carboxamide (50.0 mg, 0.13 mmol), <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (18.0 mg, 0.16 mmol), 1H-benzo[d][1,2,3]triazol- 1-ol (35.0 mg, 0.26 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (50.0 mg, 0.26 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 16 hours. Water (20 mL) was added and the mixture was extracted with 2x 30 mL portions of dichloromethane. The organic layers were pooled and concentrated under reduced pressure. Crude product was purified by prep-HPLC (the crude samples were dissolved in N,N-dimethylformamide before purification. Boston pHlex ODS 10um 21.2×250mm 120A. The mobile phase was acetonitrile/0.1% ammonium bicarbonate) to afford product 1-(bicyclo[1.1.1]pentane-1-carbonyl)-N-(6-ethylbenzo[d]thiazol-2-yl)-N-(pyridin-3- ylmethyl)piperidine-4-carboxamide (38.7 mg, 0.082 mmol, 62 %) as a white solid.1H NMR (400 MHz, Dimethylsulfoxide-d6) δ 8.58 (s, 1H), 8.49 (d, J = 4.7 Hz, 1H), 7.82 (s, 1H), 7.66 - 7.62 (m, 2H), 7.36 (dd, J = 7.9, 4.8 Hz, 1H), 7.28 (d, J = 8.4, Hz, 1H), 5.70 (s, 2H), 4.28 (d, J = 12.9 Hz, 1H), 4.13 (d, J = 13.9 Hz, 1H), 3.30 - 3.19 (m, 1H), 3.06 (t, J = 11.9 Hz, 1H), 2.71 (q, J = 7.5 Hz, 2H), 2.59 (t, J = 12.8 Hz, 1H), 2.44 (s, 1H), 2.22 - 1.96 (m, 6H), 1.71 (t, J = 16.1 Hz, 2H), 1.48 (dd, J = 30.6, 11.4 Hz, 2H), 1.22 (t, J = 7.6 Hz, 3H); LCMS (ESI) m/z: 475.2 [M+H]+.

Reference： [1]Patent: WO2021/247921,2021,A1 .Location in patent: Page/Page column 205-206

20
[ 22287-28-1 ]
6-ethyl-N-(pyridin-3-ylmethyl)benzo[d]thiazol-2-amine [ No CAS ]
N-(6-ethyl-1,3-benzothiazol-2-yl)-N-[(pyridin-3-yl)methyl]bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		A solution of <strong>[22287-28-1]bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (67.0 mg, 0.60 mmol) in thionyl chloride (2 mL) was stirred at 70 C for 2 hours. The reaction was concentrated under reduced pressure and re- dissolved in dichloromethane (2 mL).6-ethyl-N-(pyridin-3-ylmethyl)benzo[d]thiazol-2-amine (80.0 mg, 0.30 mmol) and N,N-diisopropylethylamine (77.0 mg, 0.60 mmol) was added to the solution at 0 C. The reaction was warmed to room temperature with stirring over 16 hours. The product was indicated present via UPLC analysis. The reaction was diluted with dichloromethane (20 mL) and washed with water (20 mL). The organic layer separated and concentrated under reduced pressure. Crude product was purified by Prep-HPLC (the crude samples were dissolved in N,N-dimethylformamide before purification. Boston C1821*250mm 10µm column. The mobile phase was acetonitrile/0.01% aqueous formic acid) obtaining N-(6-ethylbenzo[d]thiazol-2-yl)-N-(pyridin-3-ylmethyl)bicyclo[1.1.1]pentane-1-carboxamide (24.0 mg, 0.070 mmol, 22 %) as white solid.1H NMR (400 MHz, Dimethylsulfoxide-d6) δ 8.52 - 8.38 (m, 2H), 7.82 (s, 1H), 7.60 (d, J = 8.3 Hz, 1H), 7.54 (d, J = 7.9 Hz, 1H), 7.35 (dd, J = 7.8, 4.8 Hz, 1H), 7.25 (dd, J = 8.4, 1.6 Hz, 1H), 5.64 (s, 2H), 2.70 (q, J = 7.5 Hz, 2H), 2.44 (s, 1H), 2.13 (s, 6H), 1.21 (t, J = 7.6 Hz, 3H); LCMS (ESI) m/z: 364.2 [M+H]+.

Reference： [1]Patent: WO2021/247921,2021,A1 .Location in patent: Page/Page column 135-136

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[ CAS No. 22287-28-1 ] {[proInfo.proName]}

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[ 22287-28-1 ] Synthesis Path-Upstream 1~1

[ 22287-28-1 ] Synthesis Path-Downstream 1~20

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Aliphatic Cyclic Hydrocarbons

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