[ CAS No. 303752-38-7 ] {[proInfo.proName]}

Name: 303752-38-7|3-(Boc-amino)bicyclo[1.1.1]pentane-1-carboxylic Acid|97%
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Quality Control of [ 303752-38-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 303752-38-7 ]

CAS No. :	303752-38-7	MDL No. :	MFCD09971715
Formula :	C₁₁H₁₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CKXLBAVWWJDBHS-UHFFFAOYSA-N
M.W :	227.26	Pubchem ID :	12085063
Synonyms :

Calculated chemistry of [ 303752-38-7 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	56.83
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	0.79
Log Po/w (WLOGP) :	1.52
Log Po/w (MLOGP) :	1.03
Log Po/w (SILICOS-IT) :	0.93
Consensus Log Po/w :	1.25

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.42
Solubility :	8.71 mg/ml ; 0.0383 mol/l
Class :	Very soluble
Log S (Ali) :	-1.96
Solubility :	2.5 mg/ml ; 0.011 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.57
Solubility :	6.1 mg/ml ; 0.0269 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.62

Safety of [ 303752-38-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 303752-38-7 ]

* 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 [ 303752-38-7 ]

[ 303752-38-7 ] Synthesis Path-Downstream 1~85

1
[ 616-34-2 ]
[ 303752-38-7 ]
methyl [3-(tert-butoxycarbonylamino)bicyclo[1.1.1]pent-1-yl]carbonyl}glycinate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

2
[ 76-05-1 ]
[ 303752-38-7 ]
3-amino-bicyclo[1.1.1]pentane-1-carboxylic acid; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

3
[ 303752-38-7 ]
methyl 3-aminobicyclo[1.1.1]pentane-1-carboxylate hydrochloride [ No CAS ]
methyl 3-{N-[3'-N-(tert-butoxycarbonyl)aminobicyclo[1.1.1]pent-1'-yl-carbonyl]amino}bicyclo[1.1.1]pentane-1-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

4
[ 676371-64-5 ]
[ 303752-38-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 20℃;	To a solution of methyl 3 -((tert-butoxycarbonyl)amino)bicyclo [1.1.1 ]pentane- 1- carboxylate intermediate 36 (850 mg, 3.52 mmol) in tetrahydrofuran (10 mL), methanol (3 mL) and water (3 mL) was added lithium hydroxide monohydrate (296 mg, 7.04 mmol). After stirred at room temperature overnight, the mixture was poured into water (30 mL) and adjusted pH to 3 - 4 with 1 M hydrochloride aqueous solution (8mL). The obtained aqueous solution was extracted with ethyl acetate (20 mL) for three times. The combined organic layers were dried over Na2SO4(), filtered and concentrated to give the title product (720 mg, 90 % yield) as white solids. LC-MS (ESI): RT = 0.66 1 mm, mass calcd. for C,,H,7N04 227.1, mlz found 226.0 [M-Hf. ?H NIVIR (300 1VIHz, DMSO-d6) 12.35 (s, 1H), 7.58 (s, 1H), 2.10 (s, 6H), 1.37 (s, 9H).
89%	With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 0 - 20℃;	[0253] To a solution of Compound 11-1 (3.05g, 12.6mmol) in THF (21. ImL), MeOH (21. ImL), and H20 (21. ImL) at 0C was added LiOH H20 (1.59g, 37.9mmol). The reaction was warmed to rt and stirred overnight. The reaction was concentrated in vacuo to remove THF and MeOH and then diluted with water to 50mL. The aqueous layer was washed with Et20 and then acidified to pH 3 with IN HC1. The aqueous layer was extracted with EtOAc (3X50 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to provide 3-((tert- butoxycarbonyl)amino)bicyclo[l. l. l]pentane-l-carboxylic acid 11-2 (2.56g, 89%) as a white solid. LC/MS (APCI) mlz 128.0 [CiiHi7N04-C5H902+H]+.
	With water; sodium hydroxide; In tetrahydrofuran; methanol; at 25℃; for 12h;	General procedure: General Procedure for the Synthesis of Cubane and Propellane Carboxyhc Acids 22-25: To a stirred solution of the corresponding methyl carboxylate (0.5 mmol) in THF (3.8 mL) at 25 C was added dropwise a solution of NaOH (0.024 g, 0.6 mmol) in MeOH (0.4 mL) dropwise and the reaction mixture was stirred at the same temperature for 12 h. The solvent was removed under reduced pressure and the obtained residue was dissolved in H20 (5 mL). The two layers were separated, and the aqueous layer was extracted with EtOAc (3 chi 30 mL). The combined organic layers were dried with anhydrous Na2S04. The solvent was evaporated to give the corresponding carboxyhc acid as white solids. The crude carboxyhc acids were used for the next reaction without further purification. 3-((fert-Butoxycarbonyl)amino)bicyclo[l.l.l]pentane-l-carboxylic acid (22): According to the general procedure described for the synthesis of propaellane carboxyhc acids, carboxyhc acid 22 was obtained as white solid (118.2 mg, 98%).

	With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 25℃; for 12h;Inert atmosphere;	103251 To a mixture of methyl 3-Qert-butoxycarbonylamino)bicyclo[1.1.ljpentane-1-carboxylate (500 mg, 2.07 mmol) in THF (10 mL) and water (2 mL) was added LiOH?H20 (173 mg, 4.14 mmol) at 25 C under N2. The mixture was stirred at 25 C for 12 h. To the mixture was added water (10 mL). The aqueous phase was extracted with MTBE (5 mL). The combined organic phase was adjusted to pH = 2 by HC1 (2M) and extracted with CH2C12:MeOH (3 x 10 mL, v:v = 3:1) and washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product. ?H-NMR (400 MHz, DMSO-d6): 7.54 (s, 1 H), 2.05 (s, 6 H), 1.34 (s, 9 H).
	With water; lithium hydroxide; In tetrahydrofuran; methanol; at 15℃; for 15h;	To a solution of methyl 3-((tert-butoxycarbonyl)amino)bicyclo[l . l . l]pentane-l- carboxylate (3 g, 12.43 mmol) in MeOH (16 mL), THF (16 mL) and water (5 mL) was added lithium hydroxide (0.893 g, 37.3 mmol) at ~ 15 C. After the addition was complete, the reaction was stirred at the same temperature. The reaction was monitored by TLC (Pet. ether: EtOAc=3 : l). After stirring at 15 C for 15 h, the reaction was finished. The reaction was cooled to 0 C, diluted with water (30 mL), acidified by 1N HC1 to pH ~ 6, and extracted with EtOAc (40 mLx 4). The organic layer was separated, dried over Na2S04 and filtered. The filtrate was concentrated to afford the title compound as a solid, which was used in the next step without further purification. 1H NMR (400 MHz, CD3OD) d 2.21 (s, 6 H) 1.44 (br s, 9 H)

Reference： [1]Patent: WO2019/1420,2019,A1 .Location in patent: Page/Page column 54; 55
[2]Patent: WO2018/213140,2018,A1 .Location in patent: Paragraph 0252
[3]European Journal of Organic Chemistry,2004,p. 493 - 498
[4]European Journal of Organic Chemistry,2017,vol. 2017,p. 6450 - 6456
[5]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708
[6]Patent: WO2016/138288,2016,A1 .Location in patent: Page/Page column 109
[7]Patent: WO2019/32743,2019,A1 .Location in patent: Paragraph 0218; 0325
[8]Patent: WO2019/60365,2019,A1 .Location in patent: Paragraph 0254
[9]Patent: WO2019/204180,2019,A1 .Location in patent: Page/Page column 80

5
[ 83249-10-9 ]
[ 303752-38-7 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498
[2]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708
[3]Patent: WO2016/138288,2016,A1
[4]Patent: WO2018/213140,2018,A1
[5]Patent: WO2019/1420,2019,A1
[6]Patent: WO2019/204180,2019,A1

6
[ 83249-09-6 ]
[ 303752-38-7 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

8
[ 303752-38-7 ]
H₂N-bicyclo[1.1.1]pentane-L-Tyr(O-t-Bu)-L-Leu-OMe [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

9
[ 303752-38-7 ]
H₂N-Gly-bicyclo[1.1.1]pentane-L-Met-L-Asp(Ot-Bu)-L-Phe-COOH [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

10
[ 303752-38-7 ]
[ 676371-75-8 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

11
[ 303752-38-7 ]
Fmoc-L-Ala-bicyclo[1.1.1]pentane-L-Tyr(O-t-Bu)-L-Leu-OMe [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

12
[ 303752-38-7 ]
H₂N-bicyclo[1.1.1]pentane-L-Met-Gly-L-Trp(Boc)-L-Met-L-Asp(Ot-Bu)-L-Phe-COOH [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 493 - 498

13
[ 1453198-99-6 ]
[ 303752-38-7 ]
tert-butyl (3-((3-((5-chloro-4-(1-(phenylsulfonyl)-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl)carbamoyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine; 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 3h;	To a solution Nl-(5-chloro-4-(l-(phenylsulfonyl)-lH-indol-3-yl)pyrimidin-2-yl)benzene- 1,3-diamine (17.8 mg, 0.0374 mmol) in DMF (748 mu) was added Et3N (18 mu,, 0.123 mmol), 3- ((tert-butoxycarbonyl)amino)bicyclo[l.l. l]pentane-l-carboxylic acid (18.7 mg, 0.0411 mmol) and HATU (15.6 mg, 0.0411 mmol). The mixture was stirred for 3h at rt, then diluted with dichloromethane (5 mL) and extracted twice with water. The organic portion was washed with brine (5 mL), then dried over sodium sulfate, filtered and concentrated. The crude residue was purified by Si02 chromatography (0-20% MeOH/DCM gradient) to afford the title compound (12.8 mg, 0.00934 mmol, 50%) as an off-white solid.

Reference： [1]Patent: WO2015/154039,2015,A2 .Location in patent: Paragraph 415; 416

14
[ 303752-38-7 ]
N-[(±)-3-[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]amino}cyclohexyl]-3-(prop-2-enamido)bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/154039,2015,A2

15
[ 303752-38-7 ]
3-amino-N-[(±)-3-[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]amino}cyclohexyl]bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/154039,2015,A2

16
[ 303752-38-7 ]
C₃₀H₃₁ClN₆O₃S [ No CAS ]

Reference： [1]Patent: WO2015/154039,2015,A2

17
(±)-N1-(5-chloro-4-(1-(phenylsulfonyl)-1H-indol-3-yl)pyrimidin-2-yl)cyclohexane-1,3-diamine hydrochloride [ No CAS ]
[ 303752-38-7 ]
tert-butyl (3-(((±)-3-((5-chloro-4-(1-(phenylsulfonyl)-1H-indol-3-yl)pyrimidin-2-yl)amino)cyclohexyl)carbamoyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With triethylamine; 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;	To a solution of (±)-Nl-(5-chloro-4-(l-(phenylsulfonyl)-lH-indol-3-yl)pyrimidin-2- yl)cyclohexane-l,3-diamine.HCl (80 mg, 0.155 mmol) in DMF (1.1 mL) was added Et3N (65 mu, 0.466 mmol,), 3-((tert-butoxycarbonyl)amino)bicyclo[l.l. l]pentane-l-carboxylic acid (53 mg, 0.233 mmol) and HATU (88 mg, 0.233 mmol). The mixture was stirred for 2h at rt, then diluted with dichloromethane (5 mL) and extracted twice with water. Organic portion was washed with brine (5 mL), then dried over sodium sulfate, filtered and concentrated. The crude residue was purified by Si02 chromatography (0-100% EtOAc/DCM gradient) to afford the title compound (45 mg, 0.065 mmol, 42%) as an off-white solid.

Reference： [1]Patent: WO2015/154039,2015,A2 .Location in patent: Paragraph 407; 408

18
C₃₁H₄₄N₄O₆S [ No CAS ]
[ 303752-38-7 ]
C₄₂H₅₉N₅O₉S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708

19
methyl (2S,4R)-4-[(2-{(1R,3R)-1-(acetyloxy)-3-[L-isoleucyl(methyl)amino]-4-methylpentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate [ No CAS ]
[ 303752-38-7 ]
C₄₃H₆₃N₅O₉S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708

20
[ 303752-38-7 ]
methyl (2S,4R)-4-(2-((1R,3R)-3-((2S,3S)-2-(3-acetamidobicyclo[1.1.1]pentane-1-carboxamido)-N,3-dimethylpentanamido)-1-acetoxy-4-methylpentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708

21
[ 303752-38-7 ]
C₃₈H₅₅N₅O₇S*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708

22
[ 303752-38-7 ]
C₃₇H₅₁N₅O₇S*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708

23
[ 303752-38-7 ]
methyl (2S,4R)-4-(2-((1R,3R)-3-((S)-2-(3-acetamidobicyclo[1.1.1]pentane-1-carboxamido)-2-cyclopropyl-N-methylacetamido)-1-acetoxy-4-methylpentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708

24
[ 303752-38-7 ]
[ 543-27-1 ]
C₁₆H₂₅NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at -20℃; for 0.5h;	Methyl 2-(3-((tert-butoxycarbonyl)amino)bicyclo[l.l.l]pentan-l-yl)acetate (79b): To a stirred solution of 3-((teri-butoxycarbonyl)amino)bicyclo[l. l. l]pentane-l-carboxylic acid 22 (10 mg, 0.04 mmol) and Et3N (0.006 niL) in THF (1 niL) at -20 C was added isobutyl Chloroformate (0.006 mL, 0.05 mmol). After stirring for 30 min at the same temperature, precipitated Et3NH+Cl" was filtered off. Acetonitrile (0.5 mL) and TMSCHN2 (2 in hexane, 0.04 mL, 0.08 mmol) were added to the filtrate at -20 C and the mixture was stirred for 18 h, allowing the temperature to gradually rise to room temperature. Diethyl ether (5 mL) was then added and the mixture was extracted with 10% aqueous citric acid and saturated NaHCCh. Combined organic extracts were dried over Na2SC>4 and evaporated under reduced pressure. The obtained residue was purified by flash column chromatography (silica gel, 10?80% EtOAc in hexanes) to afford diazoketone 79a (quantitative yield) as a yellowish solid. 79a: Rf = 0.3 (silica gel, 50% EtOAc in hexanes); NMR: (CDC13, 600 MHz) delta = 5.29 (s, 1H), 4.97 (s, 1H), 2.24 (s, 6H), 1.44 (s, 9H); 13C NMR: (CDCI3, 150 MHz) delta = 190.7, 154.7, 79.9, 54.0, 53.4, 45.3, 40.4, 28.4.

Reference： [1]Patent: WO2016/138288,2016,A1 .Location in patent: Page/Page column 167

25
[ 303752-38-7 ]
methyl 2-(3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentan-1-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2016/138288,2016,A1
[2]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711
[3]Patent: WO2019/108685,2019,A1

26
[ 303752-38-7 ]
methyl (3-[(2-{1-acetoxy-4-methyl-3-[methyl(3-methyl-2-[(1-methylpiperidin-2-yl)carbonyl]amino}-butanoyl)amino]pentyl}-1,3-thiazol-4-yl)carbonyl]amino}bicyclo[1.1.1]pent-1-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2016/138288,2016,A1
[2]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711
[3]Patent: WO2019/108685,2019,A1

27
[ 303752-38-7 ]
C₁₂H₁₇N₃O₃ [ No CAS ]

Reference： [1]Patent: WO2016/138288,2016,A1

28
[ 303752-38-7 ]
C₈H₁₃NO₂ [ No CAS ]

Reference： [1]Patent: WO2016/138288,2016,A1

29
[ 303752-38-7 ]
[ 2381-75-1 ]
tert-butyl (3-(2-(2-(4-chlorophenoxy)acetyl)hydrazine-1-carbonyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 18h;	To a solution of 3-((teri-butoxycarbonyl)amino)bicyclo[l. l . l]pentane-l-carboxylic acid (Pharmablock, 0.844 g, 3.71 mmol) in N,N-dimethylformamide (10 mL) was added N,N- diisopropylethylamine (1.3 mL, 7.43 mmol), l-[bis(dimethylamino)methylene]-lH-l,2,3- triazolo[4,5-Z>]pyridinium 3-oxid hexafluorophosphate (1.55 g, 4.09 mmol) and 2-(4- chlorophenoxy)acetohydrazide (0.82 g, 4.09 mmol). The reaction was stirred at room temperature for 18 hours and poured into water (200 mL). The precipitate was collected by filtration, washed with water and dried in a vacuum oven to provide 1.491 g (98%) of the title compound. MS (APCI) m/z 410 (M+H)+.
98%	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 18h;	To a solution of 3-(Qert-butoxycarbonyl)amino)bicyclo[ 1.1.1 Ipentane- 1 -carboxylic acid(Pharmablock, 0.844 g, 3.71 mmol) in N,N-dimethylformamide (10 mL) was added N,Ndiisopropylethylamine (1.3 mL, 7.43 mmol), 1- [bis(dimethylamino)methylenel - 1H- 1,2,3- triazolo[4,5-blpyridinium 3-oxid hexafluorophosphate (1.55 g, 4.09 mmol) and 2-(4- chlorophenoxy)acetohydrazide (0.82 g, 4.09 mmol). The reaction was stirred at room temperature for 18 hours and poured into water (200 mL). The precipitate was collected byfiltration, washed with water and dried in a vacuum oven to provide 1.49 1 g (98%) of the title compound. MS (APCI) m/z 410 (M+H).

Reference： [1]Patent: WO2017/193030,2017,A1 .Location in patent: Page/Page column 114
[2]Patent: WO2019/90078,2019,A1 .Location in patent: Page/Page column 121

30
[ 303752-38-7 ]
[ 2381-75-1 ]
tert-butyl (3-(5-((4-chlorophenoxy)methyl)-1,3,4-oxadiazol-2-yl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2017/193030,2017,A1

31
2-(3,4-dichlorophenoxy)-N-hydroxyacetimidamide [ No CAS ]
[ 303752-38-7 ]
tert-butyl (3-(3-((3,4-dichlorophenoxy)methyl)-1,2,4-oxadiazol-5-yl)bicyclo[1.1.1 ]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		A mixture of 3-((teri-butoxycarbonyl)amino)bicyclo[l . l . l]pentane-l -carboxylic acid (1.557 g, 6.85 mmol), and Iota , Gamma-carbonyldiimidazole (1.21 g, 7.47 mol) in N,N- dimethylformamide (8 mL) was stirred at room temperature for 1 hour, and then 2-(3,4- dichlorophenoxy)-N-hydroxyacetimidamide (1.69 g, 7.19 mmol, Example 59B) in N,N- dimethylformamide (4 mL) was added. The mixture was stirred at 90 C overnight. Then the N^V-dimethylformamide was removed under vacuum and ethyl acetate (100 mL) was added. The organic phase was washed with water (100 mL x 3), dried over Na2SC>4, filtered and concentrated to give 3 g of solid. The solid was dissolved in ethyl acetate (8 mL) and purified by flash column chromatography on silica gel (80 g) eluted with ethyl acetate to give 1.99 g of the title compound (68% yield) as a white solid. XH NMR (400 MHz, DMSO-i) delta ppm 7.80 (brs, 1H), 7.56 (d, J = 8, 1H), 7.39 (d, J = 2, 1H), 7.07 (dd, J = 8, 2, 1H), 5.32 (s, 2H), 2.41 (s, 6H), 1.40 (s, 9H). MS (ESI-) m/z 424 (M-H)".
68%		A mixture of 3-((tert-butoxycarbonyl)amino)bicyclo[ 1.1.1 Ipentane- 1 -carboxylic acid (1.557 g, 6.85 mmol), and 1,1?-carbonyldiimidazole (1.21 g, 7.47 mol) in N,Ndimethylformamide (8 mL) was stirred at room temperature for 1 hour, and then 2-(3,4- dichlorophenoxy)-N-hydroxyacetimidamide (1.69 g, 7.19 mmol, Example 59B) in N,Ndimethylformamide (4 mL) was added. The mixture was stirred at 90 C overnight. Then theN,N-dimethylformamide was removed under vacuum and ethyl acetate (100 mL) was added. The organic phase was washed with water (100 mL x 3), dried over Na2504, filtered and concentrated to give 3 g of solid. The solid was dissolved in ethyl acetate (8 mL) and purified by flash column chromatography on silica gel (80 g) eluted with ethyl acetate to give 1.99 g of the title compound (68% yield) as a white solid. ?H NMR (400 MHz, DMSO-d6) oe ppm 7.80(brs, 1H), 7.56 (d, J = 8, 1H), 7.39 (d, J = 2, 1H), 7.07 (dd, J = 8, 2, 1H), 5.32 (s, 2H), 2.41 (s, 6H), 1.40 (s, 9H). MS (ESI-) m/z 424 (M-H).

Reference： [1]Patent: WO2017/193030,2017,A1 .Location in patent: Page/Page column 135
[2]Patent: WO2019/90078,2019,A1 .Location in patent: Page/Page column 140

32
2-(4-chlorophenoxy)-N-hydroxyacetimidamide [ No CAS ]
[ 303752-38-7 ]
tert-butyl (3-(((2-(4-chlorophenoxy)acetimidamido)oxy)carbonyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	To a solution of Example 2A (6 g, 25.9 mmol) in N,N-dimethylformamide (120 mL) were added N-ethyl-N-isopropylpropan-2-amine (13.56 mL, 78 mmol), 2-(3H-[l,2,3]triazolo [4,5- )]pyridin-3-yl)-l,l,3,3-tetramethylisouronium tetrafluoroborate (10.00 g, 31.0 mmol) and lH-benzo[cf][l,2,3]triazol-l-ol hydrate (0.792 g, 5.17 mmol) at ambient temperature. Then 3- ((teri-butoxycarbonyl)amino)bicyclo[l.l. l]pentane-l-carboxylic acid (Pharmablock, 12.98 g, 25.9 mmol) was added to this mixture at 0 C. The mixture was stirred at ambient for 2 hours, then diluted with water (1000 mL), and the resulting mixture was extracted with ethyl acetate (3 x 350 mL). The combined organic layers were washed with brine (3 x 200 mL), dried (0573) (Na2SC>4) and concentrated under reduced pressure to provide 13 g (98%) of the title compound as a white solid. MS (APCI) m/z 410 (M+H)+.
98%	With 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	To a solution of Example 2A (6 g, 25.9 mmol) in N,N-dimethylformamide (120 mL) were added N-ethyl-N-isopropylpropan-2-amine (13.56 mL, 78 mmol), 2-(3H- [1,2,3 Itriazolo[4,5 -blpyridin-3 -yl)- 1,1,3,3 -tetramethylisouronium tetrafluoroborate (10.00 g, 31.0 mmol) and1H-benzo[dl[1,2,3ltriazol-1-ol hydrate (0.792 g, 5.17 mmol) at ambient temperature. Then 3-((tert-butoxycarbonyl)amino)bicyclo [1.1.1 Ipentane- 1 -carboxylic acid (Pharmablock, 12.98 g,25.9 mmol) was added to this mixture at 0 C. The mixture was stirred at ambient for 2 hours,then diluted with water (1000 mL), and the resulting mixture was extracted with ethyl acetate (3x 350 mL). The combined organic layers were washed with brine (3 x 200 mL), dried (Na2504)and concentrated under reduced pressure to provide 13 g (98%) of the title compound as a white solid. MS (APCI) m/z 410 (M+H).

Reference： [1]Patent: WO2017/193030,2017,A1 .Location in patent: Page/Page column 112
[2]Patent: WO2019/90078,2019,A1 .Location in patent: Page/Page column 118-119

33
2-(4-chloro-3-fluorophenoxy)acetohydrazide [ No CAS ]
[ 303752-38-7 ]
tert-butyl (3-(2-(2-(4-chloro-3-fluorophenoxy)acetyl)hydrazine-1-carbonyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	To a solution of 3-((teri-butoxycarbonyl)amino)bicyclo[l. l.l]pentane-l-carboxylic acid (Pharmablock, 2.5 g, 11.00 mmol) and Example 16A (2.66 g, 11.55 mmol) in N,N- dimethylformamide (50 mL) was added N,N-diisopropylethylamine (4.27 g, 33.0 mmol) and 2- (7-aza-lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate (6.27 g, 16.50 mmol) at 0 C, and the resulting mixture was stirred for 2 hours at ambient temperature. The mixture was diluted with water (250 mL), and the resulting mixture was extracted with ethyl acetate (3 x 200 mL). The combined organic layer was washed with brine (3 x 100 mL), dried (Na2SC>4) and concentrated under reduced pressure to provide 6 g, (89%) of the title compound as brown oil. MS (APCI) m/z 428 (M+H)+.
89%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	To a solution of 3-((tert-butoxycarbonyl)amino)bicyclo[ 1.1.1 Ipentane- 1 -carboxylic acid (Pharmablock, 2.5 g, 11.00 mmol) and Example 16A (2.66 g, 11.55 mmol) in N,Ndimethylformamide (50 mL) was added N,N-diisopropylethylamine (4.27 g, 33.0 mmol) and 2- (7-aza- 1H-benzotriazole- l-yl)-l,l,3 ,3-tetramethyluronium hexafluorophosphate (6.27 g, 16.50 mmol) at 0 C, and the resulting mixture was stirred for 2 hours at ambient temperature. Themixture was diluted with water (250 mL), and the resulting mixture was extracted with ethyl acetate (3 x 200 mL). The combined organic layer was washed with brine (3 x 100 mL), dried (Na2504) and concentrated under reduced pressure to provide 6 g, (89%) of the title compound as brown oil. MS (APCI) m/z 428 (M+H).
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; at 20 - 80℃; for 12h;Inert atmosphere;	To a mixture of 3-(tert-butoxycarbonylamino)bicyclo[1.1. ljpentane-1-carboxylic acid (50 mg, 0.22 mmol) and 2-(4-chloro-3-fluoro-phenoxy)acetohydrazide (48 mg, 0.22 mmol in EtOAc (5 mL) was added T3P (420 mg, 0.66 mmol, 50% in EtOAc) and NEt3 (89 mg, 0.88 mmol) at 20C under N2. The mixture was stirred at 80 C for 12 h. The mixture was poured into aq. NaHCO3 (10 mL). The aqueous phase was extracted with EtOAc (3 x 5 mL). The combined organic phase was washed with brine (5 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product.

Reference： [1]Patent: WO2017/193030,2017,A1 .Location in patent: Page/Page column 118; 119
[2]Patent: WO2019/90078,2019,A1 .Location in patent: Page/Page column 125
[3]Patent: WO2019/32743,2019,A1 .Location in patent: Paragraph 0218; 0326

34
[ 303752-38-7 ]
benzyl (3-azidobicyclo[1.1.1]pent-1-yl)carbamate [ No CAS ]

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

35
[ 303752-38-7 ]
tert-butyl (3-(hydroxymethyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

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

36
[ 303752-38-7 ]
tert-butyl N-(1-ethynyl-3-bicyclo [1.1.1]pentanyl)carbamate [ No CAS ]

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

37
[ 303752-38-7 ]
tert-butyl N-(1-amino-3-bicyclo[1.1.1]pentanyl)carbamate [ No CAS ]

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

38
[ 303752-38-7 ]
tert-butyl [3-(1-benzyl-1H-1,2,3-triazol-4-yl)bicyclo[1.1.1]pent-1-yl]carbamate [ No CAS ]

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

39
[ 303752-38-7 ]
benzyl (3-aminobicyclo[1.1.1]pent-1-yl)carbamate [ No CAS ]

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

40
[ 303752-38-7 ]
tert-butyl (3-formyl bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

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

41
[ 303752-38-7 ]
tert-butyl (3-azidobicyclo[1.1.1]pent-1-yl)carbamate [ No CAS ]

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

42
[ 303752-38-7 ]
[ 100-51-6 ]
benzyl tert-butyl bicyclo[1.1.1]pentane-1,3-diyldicarbamate [ No CAS ]

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

43
[ 303752-38-7 ]
tert-butyl 3-cyanobicyclo[1.1.1]pentan-1-ylcarbamate [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1
[2]Patent: WO2019/126505,2019,A1

44
[ 24424-99-5 ]
3-aminobicyclo[1.1.1]pentane-1-carboxylic acid hydrochloride [ No CAS ]
[ 303752-38-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water;	A mixture of 3-aminobicyclo[1.1.1]pentane-1-carboxylic acid, HCl (500.0 mg, 3.06 mmol, PharmaBlock) and N,N-diisopropylethylamine (1.0 mL, 6.1 mmol) in THF (10 mL) and water (10 mL) was treated with di-tert-butyl dicarbonate (667 mg, 3.06 mmol). After stirring overnight, the reaction was treated with 1 N HCl to achieve pH 2 and was extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over Na2SO4, filtered and concentrated to afford a white solid (665 mg, 96%). LCMS for C11H17NO4Na (M+Na)+: calculated m/z=250.1; found 250.1.

Reference： [1]Patent: US2018/9816,2018,A1 .Location in patent: Paragraph 1052; 1053

45
[ 303752-38-7 ]
tert-butyl (3-carbamoylbicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		A solution of <strong>[303752-38-7]3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (660 mg, 2.90 mmol) in THF (15 mL) was treated with triethylamine (0.49 mL, 3.5 mmol). The resulting mixture was cooled to -15 C. and ethyl chloroformate (0.31 mL, 3.2 mmol) was added and the mixture was stirred for 1 h. To the mixture was added ammonium hydroxide (19.5 mL, 145 mmol) solution. After stirring for 3 hours, THF was evaporated and to the white crude solid was added water. The aqueous suspension was extracted with EtOAc (3*). The combined organic extracts (fine suspension) were dried over Na2SO4, and decanted (rather than filtered). The liquid decanted was concentrated to afford a white solid (0.65 g, 100%). LCMS for C11H18N2O3Na (M+Na)+: calculated m/z=249.1, found 249.2. 1H NMR (400 MHz, DMSO-d6) delta 7.50 (br s, 1H), 7.21 (s, 1H), 6.91 (s, 1H), 2.02 (s, 6H), 1.38 (s, 9H).
100%		A solution of <strong>[303752-38-7]3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (660 mg, 2.90 mmol) in THF (15 mL) was treated with triethylamine (0.49 mL, 3.5 mmol). The resulting mixture was cooled to -15 C and ethyl chloroformate (0.31 mL, 3.2 mmol) was added and the mixture was stirred for lh. To the mixture was added ammonium hydroxide (19.5 mL, 145 mmol) solution. After stirring for 3 hours, THF was evaporated and to the white crude solid was added water. The aqueous suspension was extracted with EtOAc (3x). The combined organic extracts (fine suspension) were dried over Na2SC>4, and decanted (rather than filtered). The liquid decanted was concentrated to afford a white solid (0.65 g, 100%). LCMS for CnHigNzOsNa (M+Na)+: calculated m/z = 249.1, found 249.2. NMR (400 MHz, DMSO-de) d 7.50 (br s, 1H), 7.21 (s, 1H), 6.91 (s, 1H), 2.02 (s, 6H), 1.38 (s, 9H).
		Isobutyl chloroformate (539 tL, 4.16 mmol) was added via syringe to a stirred mixture of N,N-diisopropylethylamine (773 iL, 4.44 mmol) and 3-((tert- butoxycarbonyl)amino)bicyclo[1. 1. ljpentane-1-carboxylic acid (630 mg, 2.77 mmol) in tetrahydrofuran (20 mL) at ambient temperature. After 60 mm, the resulting mixture was cooled to 0C. Ammonia solution (0.4 M in tetrahydrofuran, 20.8 mL, 8.32 mmol) and N,Ndiisopropylethylamine (773 tL, 4.44 mmol) were added sequentially via syringe. After 15 mm, the resulting mixture was warmed to ambient temperature. After 80 mm, the reaction mixture was purified by flash column chromatography on silica gel (0 to 15% methanol in dichloromethane) to give tert-butyl (3-carbamoylbicyclo[1. 1. ljpentan-1-yl)carbamate.

Reference： [1]Patent: US2018/9816,2018,A1 .Location in patent: Paragraph 1054; 1055
[2]Patent: WO2019/126505,2019,A1 .Location in patent: Page/Page column 79
[3]Patent: WO2018/39531,2018,A1 .Location in patent: Paragraph 0421

46
[ 303752-38-7 ]
3-aminobicyclo[1.1.1]pentane-1-carbonitrile hydrochloric acid salt [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

47
[ 303752-38-7 ]
3-(4-aminoimidazo[2,1-f][1,2,4]triazin-7-yl)-N-(3-cyanobicyclo[1.1.1]pentan-1-yl)-4-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

48
4-((tert-butoxycarbonyl)amino)bicyclo[2.1.1]hexane-1-carboxylic acid [ No CAS ]
[ 303752-38-7 ]

Yield	Reaction Conditions	Operation in experiment
88%		A solution of 4-((tert-butoxycarbonyl)amino)bicyclo[2.1.1]hexane-1-carboxylic acid (250 mg, 1.04 mmol) (Spirochem catalog No. SPC-a643) and triethylamine (0.17 mL, 1.2 mmol) in THF (5 mL) at -15 C. was treated with ethyl chloroformate (0.109 mL, 1.14 mmol) and the reaction was stirred for 1 hour. To the mixture was added ammonium hydroxide (14.8 M, 7.0 mL, 52 mmol) in one portion. The reaction mixture was stirred at room temperature overnight. THF was evaporated, and to the white crude solid was added water. The aqueous suspension was extracted with EtOAc (3*). The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford product as a white solid (219 mg, 88%). LCMS for C12H21N2O3 (M+H)+: calculated m/z=241.2, found 241.3. 1H NMR (400 MHz, DMSO-d6) delta 7.30 (br s, 1H), 7.07 (s, 1H), 6.83 (s, 1H), 1.93 (br, 2H), 1.70 (s, 4H), 1.49 (s, 2H), 1.38 (s, 9H).

Reference： [1]Patent: US2018/9816,2018,A1 .Location in patent: Paragraph 1062; 1063

49
[ 303752-38-7 ]
[ 18107-18-1 ]
C₁₂H₁₇N₃O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711

50
[ 303752-38-7 ]
C₈H₁₃NO₂*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711
[2]Patent: WO2019/108685,2019,A1

51
[ 303752-38-7 ]
tert-butyl (3-(2-(trifluoromethyl)pyrimidin-4-yl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2018/213140,2018,A1

52
[ 75-16-1 ]
[ 303752-38-7 ]
tert-butyl (3-acetylbicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	In diethyl ether; at -5 - 20℃;	[0254] A solution of Compound 11-2 (l.Olg, 4.44mmol) in Et20 (22.2mL) was cooled to 50C and treated with MeMgBr (3.0M in Et20, 4.90mL, 14.6mmol). After 30 min, the reaction was warmed to rt. After 16h, the reaction was cooled to 0C and quenched with sat. aqueous NH4C1 solution (5mL). Upon warming to rt the reaction was diluted with DCM and H20. The combined organic layers were dried (Na2S04) and concentrated under reduced pressure to afford tert-butyl (3-acetylbicyclo[1.1.1]pentan-l-yl)carbamate 11-3 (522 mg, 52%) as a white solid. LC/MS (APCI) mlz 126.1 [Ci2Hi9N03-C5H902+H]+.

Reference： [1]Patent: WO2018/213140,2018,A1 .Location in patent: Paragraph 0254

53
[ 367-31-7 ]
[ 303752-38-7 ]
3-(5-fluoro-1H-benzo[d]imidazol-2-yl)bicyclo[1.1.1]pentan-1-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With hydrogenchloride; In water; at 160℃; for 0.833333h;Microwave irradiation;	[0275] A solution of 2-amino-4-fluoroaniline (0.278g, 2.20mmol) and 3-((tert- butoxycarbonyl)amino)bicyclo[l. l. l]pentane-l-carboxylic acid (0.500g, 2.20mmol) in a IN aqueous HCl (l l.OmL) was microwaved at 160C for 50 minutes. The dark mixture was filtered through a plug of Ci8 silica gel and washed with ACN. The filtrate was concentrated to provide the crude product which was further purified by flash chromatography (Ci8 Si02, H20/ACN buffered with 0.1% formic acid) to afford the desired product. The material was re-dissolved in EtOAc/Et20 and treated with 2N HCl in ether to generate the HCl salt. The resulting precipitate was collected via filtration and washed with Et20 to provide 0.250g (45%) of Compound 17 as an off-white solid. lU NMR (400 MHz, DMSO-J6) delta 9.17 (br s, NH, 3H), 7.76 (dd, =4.5, 8.9 Hz, 1H), 7.60 (dd, =2.3, 8.7 Hz, 1H), 7.36 (dt, =2.3, 9.4 Hz, 1H), 2.60 (s, 6H); LC/MS (APCI) mlz 218.1 [Ci2Hi2FN3+H]+.

Reference： [1]Patent: WO2018/213140,2018,A1 .Location in patent: Paragraph 0275

54
[ 4274-38-8 ]
[ 303752-38-7 ]
3-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)bicyclo[1.1.1]pentan-1-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With hydrogenchloride; In water; at 160℃; for 1h;Microwave irradiation;	[0265] A solution of 2-amino-4-(trifluoromethyl)benzenethiol hydrochloride (0.707g, 3.08mmol) and 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-l-carboxylic acid (0.700g, 3.08mmol) in IN aqueous HC1 (15.4mL) was microwaved at 160C for 60 minutes. The mixture was concentrated and diluted with EtOAc (50mL) and water (20mL). The mixture was neutralized with saturated aqueous NaHC03 (30mL) and extracted with EtOAc (4x30mL). The combined organics were dried (Na2S04) and concentrated to provide a yellow residue which was further purified by flash chromatography (Si02, DCM/0-10% MeOH containing 7N NH3) to provide a pale-yellow oil that solidified upon standing. The material was re-dissolved in EtOAc/Et20 and treated with 2N HC1 in Et20 to generate the HC1 salt. The resulting precipitate was collected via filtration and washed with Et20 to provide lOOmg (10%) of Compound 14 as an off-white solid. XH NMR (400 MHz, DMSO- d6) delta 9.01 (br s, NH, 3H), 8.39-8.35 (m, 3H), 7.79 (dd, 7=1.7, 8.5 Hz, 1H), 2.52 (s, 6H); LC/MS (APCI) mlz 285.0 [Ci3HnF3N2S+H]+.

Reference： [1]Patent: WO2018/213140,2018,A1 .Location in patent: Paragraph 0295

55
6,6’-(((2,2’-dimethyl-[1,1‘-biphenyl]-3,3’-diyl)bis(methylene))bis(oxy))bis(5-chloro-2-methoxynicotinaldehyde) [ No CAS ]
[ 303752-38-7 ]
C₄₂H₄₄Cl₂N₄O₈*2C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Trifluoroacetic acid (0.8 mL) was added to a stirred solution of 3-((tert-butoxycarbonyl)amino)bicyclo[1.1. ljpentane-1-carboxylic acid (87.9 mg, 0.387 mmol) in dichloromethane (2.0 mL) at room temperature. After 25 mm, the resulting mixture was concentratedunder reduced pressure. 6,6?-(((2,2?-Dimethyl-[ 1,1 ?-biphenyll -3,3 ?-diyl)bis(methylene))bis(oxy))bis(5 - chloro-2-methoxynicotinaldehyde) (15 mg, 0.026 mmol), 1VN-diisopropylethylamine (0.135 mL, 0.774 mmol), N,N-dimethylformamide (1.5 mL), and acetic acid (0.2 mL) were added sequentially, and the resulting mixture was stirred at room temperature. After 5 mm, sodium triacetoxyborohydride (54.7, 0.25 8 mmol) was added. After 7 mi trifluoroacetic acid (0.2 mL) was added. The resulting mixture waspurified by reverse phase preparative HPLC (0.1% trifluoroacetic acid in acetonitrile/water) to give 3,3?-((((((2,2?-dimethyl-[ 1,1 ?-biphenyll -3,3 ?-diyl)bis(methylene))bis(oxy))bis(S -chloro-2-methoxypyridine-6,3 -diyl))bis(methylene))bis(azanediyl))bis(bicyclo [1.1.1 Ipentane- 1 -carboxylic acid). ?H NMR (400MHz, Methanol-d4) 7.82 (s, 2H), 7.53 - 7.39 (m, 2H), 7.23 (t, J = 7.6 Hz, 2H), 7.07 (d, J = 7.5 Hz, 2H),5.59 (s, 4H), 4.09 (s, 4H), 4.05 (s, 6H), 2.37 (s, 12H), 2.08 (s, 6H); LRIVIS: 803.1.

Reference： [1]Patent: WO2018/195321,2018,A1 .Location in patent: Page/Page column 316; 317

56
[ 303752-38-7 ]
3-aminobicyclo[1.1.1]pentane-1-carboxylic acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1h;	3-Aminobicyclo[1 .1 .1]pentane-1-carboxylic acid 39.2The solution of compound 39.1 (150 mg, 0.66 mmol) in 4M hydrochloric acid/dioxane (5 ML)was stirred at 2000 for 1 h. The mixture was concentrated to give compound 39.2 (107 mg,0.65 mmol, 99% yield, HCI salt) as a white solid.1H NMR (CD3OD, 400 MHz) O 2.34 (d, 6H).

Reference： [1]Patent: WO2018/211275,2018,A1 .Location in patent: Page/Page column 301; 302

57
[ 303752-38-7 ]
3-(((benzyloxy)carbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/211275,2018,A1

58
[ 303752-38-7 ]
tert-butyl N-[[2-[[[3-(benzyloxycarbonylamino)bicyclo[1.1.1]pentane-1-carbonyl]-[2-oxo-2-[[(3R)-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,2’-indane]-5’-yl]amino]ethyl]amino]methyl]phenyl]methyl]-N-methyl-carbamate [ No CAS ]

Reference： [1]Patent: WO2018/211275,2018,A1

59
[ 303752-38-7 ]
tert-butyl N-[[2-[[(3-aminobicyclo[1.1.1]pentane-1-carbonyl)-[2-oxo-2-[[(3R)-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,2’-indane]-5’-yl]amino]ethyl]amino]methyl]phenyl]methyl]-N-methylcarbamate [ No CAS ]

Reference： [1]Patent: WO2018/211275,2018,A1

60
[ 303752-38-7 ]
tert-butyl N-[[2-[[(3-acetamidobicyclo[1.1.1]pentane-1-carbonyl)-[2-oxo-2-[[(3R)-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,2’-indane]-5’-yl]amino]ethyl]amino]methyl]phenyl]methyl]-N-methyl-carbamate [ No CAS ]

Reference： [1]Patent: WO2018/211275,2018,A1

61
[ 303752-38-7 ]
(x)C₂HF₃O₂*C₃₄H₃₆N₆O₄ [ No CAS ]

Reference： [1]Patent: WO2018/211275,2018,A1

62
[ 303752-38-7 ]
tert-butyl N-[1-[5-[(4-chloro-3-fluorophenoxy)methyl]-1,3,4-oxadiazol-2-yl]-3-bicyclo[1.1.1]pentanyl]carbamate [ No CAS ]

Reference： [1]Patent: WO2019/32743,2019,A1

63
[ 303752-38-7 ]
C₁₄H₁₃ClFN₃O₂*(x)ClH [ No CAS ]

Reference： [1]Patent: WO2019/32743,2019,A1

64
[ 303752-38-7 ]
N-[1-[5-[(4-chloro-3-fluorophenoxy)methyl]-1,3,4-oxadiazol-2-yl]-3-bicyclo[1.1.1]pentanyl]-2-cis-[3-(trifluoromethoxy)cyclobutoxy]acetamide [ No CAS ]

Reference： [1]Patent: WO2019/32743,2019,A1

65
[ 124-63-0 ]
[ 303752-38-7 ]
(3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentan-1-yl)methyl methanesulfonate [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1 .Location in patent: Paragraph 0254

66
[ 303752-38-7 ]
C₃₈H₄₅F₃N₈O₂S [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1

67
[ 303752-38-7 ]
C₃₃H₃₇F₃N₈S [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1

68
[ 303752-38-7 ]
N-(3-((2-cyano-4-methyl-5-((7-(2-methyl-6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)methyl)-1H-indol-1-yl)methyl)bicyclo[1.1.1]pentan-1-yl)propionamide [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1

69
[ 303752-38-7 ]
C₃₆H₄₁F₃N₈OS [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1

70
[ 303752-38-7 ]
C₂₂H₂₅N₃O₃ [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1

71
[ 303752-38-7 ]
C₃₈H₄₄F₃N₇O₂S [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1

72
[ 303752-38-7 ]
C₃₃H₃₆F₃N₇S [ No CAS ]

Reference： [1]Patent: WO2019/60365,2019,A1

73
[ 303752-38-7 ]
tert-butyl (3-(5-((4-chlorophenoxy)methyl)-1,3,4-oxadiazol-2-yl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2019/90078,2019,A1

74
[ 303752-38-7 ]
3-(5-((4-chlorophenoxy)methyl)-1,3,4-oxadiazol-2-yl)bicyclo[1.1.1]pentan-1-amine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2019/90078,2019,A1

75
[ 303752-38-7 ]
N-(3-{5-[(4-chlorophenoxy)methyl]-1,3,4-oxadiazol-2-yl}bicyclo[1.1.1]pentan-1-yl)-2-(3,4-dichlorophenoxy)acetamide [ No CAS ]

Reference： [1]Patent: WO2019/90078,2019,A1

76
[ 303752-38-7 ]
[ 543-27-1 ]
[ 18107-18-1 ]
C₁₂H₁₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		To a stirred solution of 3-[(/ert-butoxycarbonyl)amino]bicyclo[l.l. l]pentane-1-carboxylic acid (Nicolaou et al, 2016) (10 mg, 44 miho. 1.0 equiv) and Et3N (6.4 m, 46 mmol, 1.05 equiv) in THF (1 mL) at -20 C was added isobutyl chloroformate (6.0 mH 46 mhio. 1.05 equiv). After stirring for 30 min at the same temperature, precipitated Et3NH+Cr was fdtered off. Acetonitrile (0.5 mL) and TMSCHN2 (2.0 M in hexane, 40 pL, 80 mhio. 2.0 equiv) were added to the filtrate at -20 C and the mixture was stirred for 18 h, allowing the temperature to gradually rise to 23 C. Diethyl ether (5 mL) was then added and the mixture was extracted with 10% aqueous citric acid and saturated NaHCCh. The combined organic extracts were dried over Na2S04 and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography (silica gel, 10 80% EtOAc in hexanes) to afford diazoketone 83a (11 mg, 44 mhio. quantitative yield) as a yellowish solid. 83a: Rf= 0.30 (silica gel, 50% EtOAc in hexanes); 'H NMR: (CDCE, 600 MHz) d 5.29 (s, 1H), 4.97 (s, 1H), 2.24 (s, 6H), 1.44 (s, 9H) ppm; I3C NMR: (CDCE, 150 MHz) d 190.7, 154.7, 79.9, 54.0, 53.4, 45.3, 40.4, 28.4.

Reference： [1]Patent: WO2019/108685,2019,A1 .Location in patent: Page/Page column 183

77
[ 303752-38-7 ]
3-aminobicyclo[1.1.1]pentane-1-carbonitrile hydrochloric acid salt [ No CAS ]

Reference： [1]Patent: WO2019/126505,2019,A1

78
[ 303752-38-7 ]
3-aminobicyclo[ 1.1.1]pentane-1-carbonitrile trifluoroacetate salt [ No CAS ]

Reference： [1]Patent: WO2019/126505,2019,A1

79
[ 303752-38-7 ]
3-(5-amino-6-(2-methylthiazol-5-yl)pyrazin-2-yl)-N-(3-cyanobicyclo[1.1.1]pentan-1-yl)-4-methylbenzenesulfonamide trifluoroacetate salt [ No CAS ]

Reference： [1]Patent: WO2019/126505,2019,A1

80
[ 67-56-1 ]
[ 303752-38-7 ]
[ 676371-64-5 ]

Yield	Reaction Conditions	Operation in experiment
	With diazomethyl-trimethyl-silane; In hexane; at 20℃; for 1h;Cooling with ice;	To a solution of <strong>[303752-38-7]3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid</strong> (208 mg, 0.92 mmol) in methanol (4.0 ml) at 0 C was added (0861) (trimethylsilyl)diazomethane solution (2.0 M in hexanes, 0.69 ml, 1.37 mmol). The ice bath was removed and the reaction mixture was stirred at room temperature for 1H. The solution was concentrated in vacuo and the resulting white solid was used without purification.

Reference： [1]Patent: WO2019/126505,2019,A1 .Location in patent: Page/Page column 107

81
[ 24424-99-5 ]
3-aminobicyclo[1.1.1]pentane-1-carboxylic acid hydrochloride [ No CAS ]
[ 303752-38-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water;	A mixture of 3-aminobicyclo[1.1.1]pentane-1-carboxylic acid, HC1 (500.0 mg, 3.06 mmol, PharmaBlock) an d AOV-d i i s o p ro p y 1 c t h y 1 am i n c (1.0 mL, 6.1 mmol) in THF (10 mL) and water (10 mL) was treated with di-tert-butyl dicarbonate (667 mg, 3.06 mmol). After stirring overnight, the reaction was treated with 1 N HC1 to achieve pH 2 and was extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over Na2SC>4, filtered and concentrated to afford a white solid (665 mg, 96 %). LCMS for CnHnNCfiNa (M+Na)+: calculated m/z = 250.1; found 250.1..

Reference： [1]Patent: WO2019/126505,2019,A1 .Location in patent: Page/Page column 78; 88-89

82
[ 6638-79-5 ]
[ 303752-38-7 ]
tert-butyl (3-(methoxy(methyl)carbamoyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	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 dichloromethane; at 15℃; for 15h;	To a solution of 3-((/er/-butoxycarbonyl)amino)bicyclo[l. l.l]pentane-l- carboxylic acid (2.8 g, 12.32 mmol) in DCM (30 mL) were added HATU (7 g, 18.41 mmol), N,O-dimethylhydroxylamine hydrochloride (1.202 g, 12.32 mmol) and DIEA (6.5 mL, 37.2 mmol) at -15 C. After the addition was finished, the reaction was stirred at 15 C. The reaction was monitored by LCMS, after stirring at 15 C for 15 h, the reaction was finished. The reaction was poured into water (20 mL) and extracted by DCM (30 mLx 3). The organic layers were collected, washed with brine (20 mL), and dried over anhydrous Na2SC>4. After filtration, the filtrate was concentrated in vacuo. The residue was purified by flash silica gel chromatography (ISCO; Agela Flash Column Silica-CS(40 g), Eluent of 0-32% Ethyl acetate/Petroleum ether gradient 40 mL/min) to afford the title compound as a solid. MS (ESI) m/z: 27l. l[M+H+]; 1H NMR (400 MHz, CD3OD) d 3.71 (s, 3 H) 3.18 (s, 3 H) 2.29 (s, 6 H) 1.44 (br s, 9 H)

Reference： [1]Patent: WO2019/204180,2019,A1 .Location in patent: Page/Page column 80-81

83
[ 303752-38-7 ]
tert-butyl (3-((methylamino)methyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2020/12339,2020,A1

84
[ 74-89-5 ]
[ 303752-38-7 ]
tert-butyl (3-(methylcarbamoyl)bicyclo[1.1.1]pentan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16.5h;	To a solution of 3-((tert-butoxycarbonyl)amino)bicyclo[1 .1 1 ]pentane-1 -carboxylic acid (300 mg, 1 .320 mmol), HOBt (222 mg, 1 .452 mmol) in dichloromethane (DCM) (10 ml_) at room temp was added EDC (278 mg, 1 .452 mmol). The reaction mixture was stirred at rt for 0.5 h. Methanamine (205 mg, 6.60 mmol) was added. The reaction mixture was stirred for 16 h at rt and then quenched with water (10 ml_). The resulting solution was extracted with dichloromethane (3 x 10 ml_) and the organic layers were combined, washed with brine (1 x 10 ml_), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford crude product. The crude product was purified by silica gel column chromatography and eluted with ethyl acetate/petroleum ether to afford the title compound as a white solid (300mg, 90% pure, 85%yield). LCMS m/z 241 .2 (M+H)+.

Reference： [1]Patent: WO2020/12339,2020,A1 .Location in patent: Page/Page column 115

85
[ 118864-75-8 ]
[ 303752-38-7 ]
[ 2654798-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid With diphenyl phosphoryl azide; triethylamine In toluene at 110℃; for 2h; Inert atmosphere; Stage #2: (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline In toluene at 110℃; for 1.5h; Inert atmosphere;	58 [0415] Example 58: (S)-N-(3-aminobicyclo[1.1.1]pentan-1-yl)-1-phenyl-3,4- dihydroisoquinoline-2(1H)-carboxamide (Compound 4135) [0416] Synthesis of tert-butyl (S)-(3-(1-phenyl-1,2,3,4-tetrahydroisoquinoline-2- carboxamido)bicyclo[1.1.1]pentan-1-yl)carbamate. [0417] Under nitrogen atmosphere, 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane- 1 -carboxylic acid (107.2 mg, 0.472 mmol) was dissolved in a mixture of toluene (dry, 5 ml) and triethylamine (99 pl_, 0.710 mmol). At room temperature, diphenylphosphoryl azide (112 mI_, 0.517 mmol) was added after which the reaction mixture was stirred at 110 °C for 2 hours. The mixture was cooled to room temperature, (S)-1 -phenyl-1, 2,3,4- tetrahydroisoquinoline (99.7 mg, 0.476 mmol) was added, and the mixture was warmed again to 110 °C. After 1.5 hour, the reaction mixture was cooled to room temperature and concentrated to dryness under reduced pressure. The residue was taken up in dichloromethane (10 ml_) and washed with aqueous HCI (1 M, 5 ml_) and aqueous NaOH (1 M, 5 ml_). The organic layer was passed through a phase-separator and the filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography (silica, 25 to 75% ethyl acetate in heptane) to give tert-butyl (S)-(3-(1- phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)bicyclo[1.1.1]pentan-1-yl)carbamate. [0418] LCMS: 99%, RT = 2.19 min., (M+H)+ = 434 (method A). 1H NMR (400 MHz, chloroform-d) d 7.32 - 7.13 (m, 9H), 6.32 (s, 1H), 5.12 - 4.66 (m, 2H), 3.63 - 3.50 (m, 2H), 2.90 (dt, J = 15.8, 6.4 Hz, 1H), 2.79 (dt, J= 15.7, 5.9 Hz, 1H), 2.28 (s, 6H), 1.44 (s, 9H).

Reference： [1]Current Patent Assignee: ARKUDA THERAPEUTICS - WO2021/127303, 2021, A1 Location in patent: Paragraph 0415-0418

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Code	Phrase
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H312	Harmful in contact with skin
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H315	Causes skin irritation
H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
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H332	Harmful if inhaled
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H341	Suspected of causing genetic defects
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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Quality Control of [ 303752-38-7 ]

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Product Details of [ 303752-38-7 ]

Calculated chemistry of [ 303752-38-7 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

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Medicinal Chemistry

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Application In Synthesis of [ 303752-38-7 ]

[ 303752-38-7 ] Synthesis Path-Downstream 1~85

Related Functional Groups of [ 303752-38-7 ]

Aliphatic Cyclic Hydrocarbons

Amides

Amines

Carboxylic Acids

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[ 303752-38-7 ]