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Quality Control of [ 78797-58-7 ]

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Product Details of [ 78797-58-7 ]

CAS No. :	78797-58-7	MDL No. :
Formula :	C₃H₉Cl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	130.02	Pubchem ID :	-
Synonyms :

Safety of [ 78797-58-7 ]

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Application In Synthesis of [ 78797-58-7 ]

* 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.

Upstream synthesis route of [ 78797-58-7 ]
Downstream synthetic route of [ 78797-58-7 ]

[ 78797-58-7 ] Synthesis Path-Upstream 1~1

1
[ 24424-99-5 ]
[ 78797-58-7 ]
[ 147621-21-4 ]

Reference： [1] Organic Letters, 2002, vol. 4, # 11, p. 1859 - 1862

[ 78797-58-7 ] Synthesis Path-Downstream 1~26

1
[ 107128-00-7 ]
[ 101-81-5 ]
[ 78797-58-7 ]

Reference： [1]Heterocycles,1986,vol. 24,p. 2467 - 2470

2
[ 24424-99-5 ]
[ 78797-58-7 ]
[ 147621-21-4 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 1859 - 1862

3
[ 40320-60-3 ]
[ 78797-58-7 ]
[ 928038-35-1 ]

Yield	Reaction Conditions	Operation in experiment
73.1%		Azetidine hydrochloride (326 mg) was added to a solution of 1-benzhydrylazetidin-3-one (750 mg) in dichloromethane (12 ml), followed by stirring at room temperature. Sodium triacetoxyborohydride (1.01 g) was added thereto, followed by stirring at room temperature for 25 hours. Sodium carbonate (until bubbling stopped), water (50 ml) and ethyl acetate (100 ml) was added to the reaction mixture. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:1, 1:2, then ethyl acetate) to give the title compound (643 mg, 73.1%) as a pale yellow solid.1H-NMR Spectrum (CDCl3) delta (ppm): 2.06 (2H, m), 2.91 (2H, m), 3.16-3.24 (7H, m), 4.35 (1H, s), 7.15 (2H, m), 7.25 (4H, m), 7.40 (4H, d, J=7.6 Hz).ESI-MS (m/z): 279[M+H]+.
73.1%		(Production Example 79) 3-(Azetidin-1-yl)-1-benzhydrylazetidine To a solution of 1-benzhydrylazetidin-3-one (750 mg) in dichloromethane (12 ml) was added azetidine hydrochloride (326 mg), followed by stirring at room temperature. Sodium triacetoxy borohydride (1.01 g) was added thereto, followed by stirring at room temperature for 25 hr. To the reaction mixture were added sodium carbonate (until bubbling stopped), water (50 ml) and ethyl acetate (100 ml). The organic layer was separated. This was washed with brine, and dried over anhydrous sodium sulfate. The organic layer after drying was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate = 1:1, 1:2, then ethyl acetate) to provide the titled compound as a pale yellow solid (643 mg,73.1 %). 1H-NMR Spectrum (CDCl3) delta (ppm): 2.06(2H, m), 2.91 (2H, m), 3.16-3.24 (7H, m), 4.35 (1H, s), 7.15 (2H, m), 7.25 (4H, m), 7.40 (4H, d, J = 7.6 Hz). ESI-MS (m/z): 279 [M+H]+.
4.7 mg		Example 22 1. Synthesis of intermediate 022-3 The intermediate 022-1 (10 g, 42.1 mmol) as raw material was dissolved in 100 mL of dichloromethane in a 250 mL three-necked flask at room temperature under a nitrogen atmosphere, and cyclobutylamine hydrochloride (4.7 g, 50.2 mmol) was added thereto. Then, the reaction was carried out for 1h at room temperature, followed by that the reaction mixture was cooled to 0C. Sodium triacetoxyborohydride (13.4 g, 63.2 mmol) was added to the reaction system in batches, and the reaction temperature was raised to room temperature and the reaction was stirred overnight. The reaction system was adjusted to pH 8-9 with anhydrous sodium carbonate aqueous solution the next day, and the mixture was extracted three times with 200 mL of methylene chloride. The organic phases were combined and washed once with 300 mL of saturated brine. The organic phases were dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (eluent: EA / PE = 1: 5) to give 4.7 g of intermediate 022-3 as a yellow oil. LCMS: 279.2.

Reference： [1]Patent: US2008/214815,2008,A1 .Location in patent: Page/Page column 13
[2]Patent: EP1889836,2008,A1 .Location in patent: Page/Page column 78; 79
[3]Patent: EP3216786,2017,A1 .Location in patent: Paragraph 0171-0173

4
[ 78797-58-7 ]
[ 7043-09-6 ]
4-(1-azetidinyl)-6-chloro-2-cyclopropylpyrimidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3077 - 3080

5
[ 78797-58-7 ]
[ 10111-08-7 ]
[ 811794-94-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at 20℃; for 22h;	To a mixture of 2-imidazoIecarboxaldehyde (3.0g) and azetidine hydrochloride (3.21g) inanhydrous tetrahydrofuran (180ml) was added sodium triacetoxyborohydride (9.99g)followed by glacial acetic acid (1.72ml). The resultant mixture was stirred at roomtemperature for 22h, after which the insoluble material was filtered and washed with ethylacetate. The filtrate was concentrated under reduced pressure and the residue purifiedusing silica SPE (eluting with DCM, methanol, methanol:20% aqueous ammonia) to givethe title compound (2.63g) as a beige solid.Gas Chromatograph Mass spectrum: Found: MH+ 138

Reference： [1]Patent: WO2004/111045,2004,A1 .Location in patent: Page 24

6
[ 41667-95-2 ]
[ 78797-58-7 ]
[ 749908-73-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With hydrogenchloride; N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 5h;Inert atmosphere;	(60a) 5-(Azetidin-1-ylcarbonyl)-2,3-dichloropyridine Commercially available <strong>[41667-95-2]5,6-dichloronicotinic acid</strong> (200 mg, 1.04 mmol) was dissolved in dichloromethane (5.0 mL), and azetidine hydrochloride (125 mg, 1.34 mmol), HATU (440 mg, 1.16 mmol) and N,N-diisopropylethylamine (0.45 mL, 2.58 mmol) were added, followed by stirring at room temperature for 5 hours under nitrogen atmosphere. 0.5N hydrochloric acid (30 mL) was added, and extraction was carried out with dichloromethane (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=60%-80%) to afford the desired compound (162 mg, yield 67%) as a colorless liquid. 1H-NMR (CDCl3, 400 MHz): delta 2.38-2.46 (2H, m), 4.25 (2H, t, J=7.6 Hz), 4.37 (2H, t, J=7.6 Hz), 8.10 (1H, d, J=2.3 Hz), 8.51 (1H, d, J=2.3 Hz).
47%		Intermediate 21: Azetidin-1-yl-(5,6-dichloropyridin-3-yl)methanone 5,6-Dichloropyridine-3-carboxylic acid (CAS no. 41667-95-2) (32 g, 0.17 mol) was suspended in DCM (500 mL) and 1M HCl in ether (0.17 L, 0.17 mol) added. Oxalyl chloride (17 mL, 0.20 mol) and then DMF (2 drops) were added and stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, azeotroped with toluene and re-dissolved into DCM (250 mL). Azetidine hydrochloride (17.5 g, 0.18 mol) was added, followed by triethylamine (51 mL, 0.37 mol) and the reaction stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure then water (500 mL) and ethyl acetate (500 mL) were added. The organic layer was separated and the aqueous phase was re-extracted with ethyl acetate (5*150 mL). The combined organics were washed with citric acid (250 mL), saturated sodium bicarbonate solution (250 mL), brine (250 mL), dried (MgSO4), filtered and evaporated under reduced pressure to give a solid which was recrystallized in ethyl acetate and dried under reduced pressure to give the product (18.2 g, 47%). 1H NMR delta (400 MHz, CDCl3) 2.34 (quintet, 2H), 4.20 (s, 2H), 4.27 (s, 2H), 8.02 (d, 1H), 8.44 (d, 1H); m/z 231 (M+H)+.
		Oxalyl chloride (1. 6ml) was added to <strong>[41667-95-2]5,6-dichloro-3-pyridinecarboxylic acid</strong> (3. 0G) and DIMETHYLFORMAMIDE (3 drops) in DCM (25ml). The mixture was stirred for Ih, concentrated in vacuo and dissolved in DCM (20ml). Triethylamine (4. 35ML) and azetidine hydrochloride (1.46g) were added and stirred for IH. The mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: DCM 1: 4) to give the sub-title compound as a solid (1.4g). 'H NMR 8 (CDC13) 8.60 (s, lH), 8.27 (s, LH), 4. 36 (t, 2H), 4.06 (t, 2H), 2.27 (PENT, 2H)

Reference： [1]Patent: EP2239253,2010,A1 .Location in patent: Page/Page column 94
[2]Patent: US2008/171734,2008,A1 .Location in patent: Page/Page column 42
[3]Patent: WO2004/74287,2004,A1 .Location in patent: Page 33

7
[ 455-86-7 ]
[ 78797-58-7 ]
[ 863505-11-7 ]

Yield	Reaction Conditions	Operation in experiment
51%		Intermediate 6: l-(3,4-Difluorobenzoyl)azetidine; Oxalyl chloride (1.05 mL, 12.0 mmol) was added to a solution of 3,4-difluorobenzoic acid (1.58 g, 10 mmol) in DCM (50 mL) containing DMF (1 drop). The reaction was stirred at ambient temperature for 16 h then evapourated to dryness. The residue was redissolved in DCM (25 mL) and azetidine hydrochloride (1.12 g, 12.0 mmol) added followed by triethylamine (4.18 mL, 30.0 mmol). The mixture was stirred at ambient temperature for 2 h then concentrated in vacuo. The residue was partitioned between ethyl acetate and IN hydrochloric acid, the organic phase washed with a saturated aqueous solution of sodium bicarbonate followed by brine, dried (MgSO4), and concentrated in vacuo. The title compound was crystallized from an ethyl acetate / hexane mixture to give a white crystalline solid (1.0 g, 51%). 1H NMR delta (CDCl3): 2.4 (m, 2H), 4.3 (m, 4H), 7.2 (m, IH), 7.4 (m, IH), 7.5 (t, IH).
51%		Intermediate 1: l-(3,4-DifluorobenzovDazetidine; Oxalyl chloride (1.05 mL, 12.0 mmol) was added to a solution of 3,4-difluorobenzoic acid (1.58 g, 10 mmol) in DCM (50 mL) containing DMF (1 drop). The reaction was stirred at ambient temperature for 16 h then evapourated to dryness. The residue was redissolved in DCM (25 mL) and azetidine hydrochloride (1.12 g, 12.0 mmol) added followed by triethylamine (4.18 mL, 30.0 mmol). The mixture was stirred at ambient temperature for 2 h then concentrated in vacuo. The residue was partitioned between ethyl acetate and IN hydrochloric acid, the organic phase washed with a saturated aqueous solution of sodium bicarbonate followed by brine, dried (MgSO4), and concentrated in vacuo. The title compound was crystallized from an ethyl acetate / hexane mixture to give a white crystalline solid (1.0 g, 51%). 1H NMR delta (CDCl3): 2.4 (m, 2H), 4.3 (m, 4H), 7.2 (m, IH), 7.4 (m, IH), 7.5 (t, IH).
		3.4-Difluorophenyr)carbonyl]azetidine; Oxalyl chloride (1.05 rnL, 12.0 mmol) was added to a solution of 3,4-difluorobenzoic acid (1.58 g, 10 mmol) in DCM (50 mL) containing DMF (1 drop). The reaction was stirred at RT for 16 hours then evapourated to dryness. The residue was redissolved in DCM (25 mL) and azetidine hydrochloride (1.12 g, 12.0 mmol) added followed by triethylamine (4.18 mL, 30.0 mmol). The mixture was stirred at RT for 2 h then concentrated in vacuo. The residue was partitioned between ethyl acetate and IN hydrochloric acid, the organic phase washed with a saturated aqueous solution of sodium bicarbonate followed by brine, dried (MgSO4), and concentrated in vacuo. The title compound was crystallized from an ethyl acetate and hexane mixture to give a white crystalline solid (1.0 g,). 1H NMR delta (CDCl3): 2.4 (m, 2H), 4.3 (m, 4H), 7.2 (m, IH), 7.4 (m, IH), 7.5 (t, IH).

Reference： [1]Patent: WO2006/40528,2006,A1 .Location in patent: Page/Page column 69
[2]Patent: WO2006/40529,2006,A1 .Location in patent: Page/Page column 66
[3]Patent: WO2007/17649,2007,A1 .Location in patent: Page/Page column 48

8
[ 105806-13-1 ]
[ 78797-58-7 ]
[ 1152110-15-0 ]

Yield	Reaction Conditions	Operation in experiment
55%		Part A: 4-Azetidino-6-hydrazino-5-fluoro-2-methylpyrimidine. 4,6-Dichloro-5-fluoro-2-methylpyrimidine (6 g, 33 mmol) was dissolved in 50 ml. of iPrOH and stirred at room temperature. Azetidine-HCI (3.25 g, 35 mmol) was added, followed by 14.4 ml. of DIPEA. The resulting reaction mixture was stirred for 3 h, and then hydrazine monohydrate was added (4.0 ml_, 82.5 mmol) and the contents were heated to 80 0C overnight. The reaction mixture was then cooled to room temperature and a precipitate formed. The precipitate was filtered, washed with iPrOH, and dried. The remaining filtrate was poured into 250 ml. of water and extracted (5 x 100 ml.) with EtOAc. The combined organic fractions were washed with water (2 x 100 ml.) and brine (2 x 100 ml_). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. This crude product was purified by flash chromatography on silica gel using 97.5/2.5/0.25 DCM/MeOH/NH4OH as the eluent. The overall combined yield of 4- azetidino-6-hydrazino-5-fluoro-2-methylpyrimidine (precipitate + chromatographed product) was 3.6 g (55%). LCMS: (M+H)+: 198.

Reference： [1]Patent: WO2009/61879,2009,A1 .Location in patent: Page/Page column 78

9
[ 67515-55-3 ]
[ 78797-58-7 ]
[ 1177420-64-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 4h;Inert atmosphere;	(54a) 1-[4-Fluoro-3-(trifluoromethyl)benzoyl]azetidine Commercially available <strong>[67515-55-3]4-fluoro-3-(trifluoromethyl)benzoic acid</strong> (230 mg, 1.10 mmol) was dissolved in dichloromethane (50 mL), and azetidine hydrochloride (120 mg, 1.28 mmol), HATU (550 mg, 1.45 mmol) and N,N-diisopropylethylamine (0.50 mL, 2.87 mmol) were added, followed by stirring at room temperature for 4 hours under nitrogen atmosphere. 0.5N hydrochloric acid (100 mL) was added, and extraction was carried out with dichloromethane (100 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=60%-80%) to afford the desired compound (211 mg, yield 78%) as a colorless liquid. 1H-NMR (CDCl3, 400 MHz): delta 2.35-2.43 (2H, m), 4.25 (2H, t, J=7.6 Hz), 4.33 (2H, t, J=7.4 Hz), 7.83-7.87 (1H, m), 7.93 (1H, dd, J=6.6, 2.0 Hz).

Reference： [1]Patent: EP2239253,2010,A1 .Location in patent: Page/Page column 89

10
[ 66909-29-3 ]
[ 78797-58-7 ]
[ 1177420-66-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;Inert atmosphere;	(61a) 5-(Azetidin-1-ylcarbonyl)-2-chloro-3-methylpyridine Commercially available <strong>[66909-29-3]6-chloro-5-methylnicotinic acid</strong> (200 mg, 1.29 mmol) was dissolved in dichloromethane (7.0 mL), and azetidine hydrochloride (160 mg, 1.71 mmol), HATU (1000 mg, 2.63 mmol) and N,N-diisopropylethylamine (0.69 mL, 3.96 mmol) were added, followed by stirring at room temperature overnight under nitrogen atmosphere. 0.5N hydrochloric acid (30 mL) was added, and extraction was carried out with dichloromethane (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=60%-75%) to afford the desired compound (160 mg, yield 64%) as a colorless liquid. 1H-NMR (CDCl3, 400 MHz): delta 2.32 (3H, s), 2.36-2.42 (2H, m), 4.24 (2H, t, J=7.6 Hz), 4.35 (2H, t, J=7.6 Hz), 7.95 (1H, dd, J=9.3, 1.0 Hz), 8.26 (1H, d, J=1.0 Hz).

Reference： [1]Patent: EP2239253,2010,A1 .Location in patent: Page/Page column 95

11
[ 403-16-7 ]
[ 78797-58-7 ]
[ 863454-79-9 ]

Yield	Reaction Conditions	Operation in experiment
		1 - IY3 -Chloro^-fluorophenvDcarbonyll azetidine; To a solution of <strong>[403-16-7]3-chloro-4-fluorobenzoic acid</strong> (1.74 g, 10.0 mmol) in DCM (50 mL) was added oxalyl chloride (1.05 mL, 12.0 mmol) and DMF (1 drop). The mixture was stirred at RT for 16 hours and the DCM and excess oxalyl chloride evaporated in vacuo. The residual acid chloride and azetidine hydrochloride (1.12 g, 12 mmol) were taken up in DCM (25 mL) and triethylamine (4.18 mL, 30 mmol) added to the mixture, which was stirred at RT for 2 hours. The DCM was evaporated in vacuo, and the residue partitioned EPO <DP n="45"/>between ethyl acetate (100 mL) and IN hydrochloric acid (50 mL). The ethyl acetate layer was washed sequentially with saturated aqueous sodium hydrogen carbonate and brine, dried (MgSO4), and evaporated. The residue was crystallized from ethyl acetate and isohexane to give the title compound (1.64 g). 1R NMR delta (CDCl3): 2.4 (m, 2H), 4.2-4.4 (m, 4H), 7.2 (m, IH), 7.55 (m, IH), 7.7 (m, IH).

Reference： [1]Patent: WO2007/17649,2007,A1 .Location in patent: Page/Page column 43-44

12
[ 4318-37-0 ]
[ 1353628-61-1 ]
[ 78797-58-7 ]
[ 1353625-26-9 ]

Yield	Reaction Conditions	Operation in experiment
		Compound 173 Intermediate 56 (105 mg, 0.21 mmol) in MeOH (2 mL) was treated with NaHC03 (175 mg, 2.1 mmol) and 1 -methyl- 1 ,4-diazepane (23 mu, 0.20 mmol) and stirred for 3 h. The solution was filtered and concentrated, then suspended in MeOH (2 mL) and treated with azetidincHCl (100 mg, 1.0 mmol) and triethylamine (300 mu, 2.1 mmol). The solution is stirred at 70 C for 18 h, then concentrated and treated to preparatory RP-HPLC (5-100% MeCN/H20, 0.1% trifluoroacetic acid modifier) to afford compound 173 (1 1 mg, 9%) as a white solid.LC-MS (ESI) mlz 602 [M + H]+, tR = 1.78 min.HPLC tR: 2.57 min.

Reference： [1]Patent: WO2011/163518,2011,A1 .Location in patent: Page/Page column 354-355

13
[ 391211-97-5 ]
[ 78797-58-7 ]
6-(azetidin-1-ylcarbonyl)-2,3-difluoro-N-(2-fluoro-4-iodophenyl)aniline [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 416 - 421

14
[ 2789-25-5 ]
[ 78797-58-7 ]
C₈H₁₀N₄O₂ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 113 - 117

15
[ 78797-58-7 ]
[ 885267-14-1 ]
[ 1437779-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;	A mixture of the pyridyl acetic acid (1.7g, 10 mmol), azetidine HCl salt (1 g, 11 mmol),HOBT (1.62 g, 12 mmol), EDCI (2.3 g, 12 mmol), and TEA(4.2 mL) in DCM (25 mL) wasstired at room temperature for 16 hours Then the reaction mixture was concentrated and the20 residue was purified by column chromatography (PE: EtOAc = 1: 1 ~ 0: 1) to give the product.25MS ESI [M + Ht 211.

Reference： [1]Patent: WO2014/52379,2014,A1 .Location in patent: Page/Page column 56

16
[ 78797-58-7 ]
[ 68886-07-7 ]
[ 1402555-51-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16.0h;	A mixture of of the phenyl acetic acid (1.7g, 10 mmol), azetidine HCl salt (1 g, 11mmol), HOBT (1.62 g, 12 mmol), EDCI (2.3 g, 12 mmol), and TEA(4.2mL) in DCM (25 mL)5 was stired at room temperature for 16 hours. Then the reaction mixture was concentrated and theresidue was purified by column chromatography (PE: EtOAc = 1:1 ~ 0:1) to give the product(500 mg, yield: 26%). MS ESI [M + Ht 210.

Reference： [1]Patent: WO2014/52379,2014,A1 .Location in patent: Page/Page column 56; 57

17
[ 458-09-3 ]
[ 78797-58-7 ]
[ 1402554-73-7 ]

Yield	Reaction Conditions	Operation in experiment
28%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;	A mixture of the phenyl acetic acid (1.7g, 10 mmol), azetidine HCl salt (1 g, 11 mmol),HOBT (1.62 g, 12 mmol), EDCI (2.3 g, 12 mmol), TEA(4.2mL) in DCM (25 mL) was stired atroom temperature for 16 hours. Then the reaction mixture was concentrated and the residue was5 purified by column chromatography (PE: EtOAc = 1: 1 ~ 0: 1) to give the desired product ( 600mg, yield: 28%). 1H NMR (400 MHz, MeOH) 8 6.99 (d, 1H), 6.87 (broads, 2H), 4.25 (t, 2H),4.05 (t, 2H), 3.38 (s, 2H), 2.29 (m, 2H). MS ESI [M + Ht 210.

Reference： [1]Patent: WO2014/52379,2014,A1 .Location in patent: Page/Page column 57; 58

18
[ 37482-64-7 ]
[ 78797-58-7 ]
2-(azetidin-1-yl)-4-ethoxy-6-methylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; caesium carbonate; In N,N-dimethyl-formamide; at 50.0℃; for 3.0h;Inert atmosphere;	To a round bottom flask containing 600 mg (3.48 mmol) of <strong>[37482-64-7]2-chloro-4-ethoxy-6-methylpyrimidine</strong>, 489 mg (5.22 mmol) of azetidine hydrochloride, 131 mg (0.69 mmol) of CuI, 164 mg (0.69 mmol) of 3,4,7,8-tetramethyl-1,10-phenanthroline and 2.83 g (8.70 mmol) of Cs2CO3 was added 15 mL of dry, degassed DMF. The reaction mixture was stirred at 50 C for 3 h. The cooled reaction mixture was filtered through Celite and the Celite pad was washed with portions of CH2Cl2. The combined organic phase was washed with water and then with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (15 * 3 cm). Elution with 19:1 hexane/EtOAc followed by 9:1 hexane/EtOAc afforded 18 as a colorless solid: yield 565 mg (84%); mp 42-43 C; silica gel TLC Rf 0.29 (3:2 hexane/EtOAc); 1H NMR (CDCl3) delta 1.24 (t, 3H, J = 7.2 Hz), 2.16 (s, 3H), 2.20 (quint, 2H, J = 7.6 Hz), 4.01 (t, 4H, J = 7.6 Hz), 4.20 (q, 2H, J = 7.2 Hz) and 5.73 (s, 1H); 13C NMR (CDCl3) delta 14.4, 16.1, 23.9, 49.9, 61.2, 95.0, 163.0, 167.7 and 170.1; mass spectrum (APCI), m/z 194.1289 (M+H)+ (C10H16N3O requires m/z 194.1293).
84%	With copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; caesium carbonate; In N,N-dimethyl-formamide; at 50.0℃; for 3.0h;	To a round bottom flask containing 600 mg (3.48 mmol) of 39, 489 mg (5.22 mmol) of azetidine hydrochloride, 131 mg (0.69 mmol) of Cul, 164 mg (0.69 mmol) of 3,4,7,8-tetramethyl- 1,10-phenanthroline and 2.83 g (8.70 mmol) of Cs2CO3 was added 15 mL of dry degassed DMF. The reaction mixture was stirred at 50 C for 3 h. The mixture was allowed to cool to room temperature and then filtered through Celite and the Celite pad was washed with CH2C12. The combined organic phase was washed with water and then with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (15 x 3 cm). Elution with 19:1 hexane-EtOAc followed by 9:1 hexane-EtOAc afforded 40 as a colorless solid:yield 565 mg (84%); mp 42-43 C; silica gel TLC Rf 0.29 (3:2 hexane-EtOAc); ?H NMR (CDC13, 400 MHz) 8 1.24 (t, 3H,J 7.2 Hz), 2.16 (s, 3H), 2.20 (quint, 2H,J 7.6 Hz), 4.01 (t, 4H,J 7.6 Hz), 4.20 (q, 2H,J= 7.2 Hz) and 5.73 (s, 1H); ?3C NMR (CDC13, 100 MHz) 6 14.4, 16.1,23.9,49.9,61.2, 95.0, 163.0, 167.7 and 170.1; mass spectrum (APCI), rn/z 194.1289 (M+H) (C,0H,6N30 requires 194.1293).

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5206 - 5220
[2]Patent: WO2016/133959,2016,A1 .Location in patent: Page/Page column 46; 47; 48

19
[ 4472-44-0 ]
[ 78797-58-7 ]
2-(azetidin-1-yl)-4,6-dimethylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 4h;Inert atmosphere;	To a stirred solution containing 655 mg (6.99 mmol) of azetidine hydrochloride, 133 mg (6.99 mmol) of CuI, and 3.42 g (10.5 mmol) of Cs2CO3 in 10 mL of dry, degassed DMF was added sequentially 500 mg (3.49 mmol) of 2-chloro-4,6-pyrimidine and 165 mg (6.99 mmol) of 3,4,7,8-tetramethyl-1,10-phenanthroline. The reaction mixture was stirred at 50 °C for 4 h. The reaction mixture was allowed to warm to room temperature and was then filtered through Celite and the Celite pad was washed with CH2Cl2. The combined organic phase was washed with water and then with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (15 * 3 cm). Elution with hexane followed by 4:1 hexane/EtOAc and then 1:1 hexane/EtOAc afforded 14 as a yellowish solid: yield 372 mg (65percent); mp 51-52 °C; silica gel TLC Rf 0.22 (3:2 hexane/EtOAc); 1H NMR (CDCl3) delta 2.20 (s, 6H), 2.24 (t, 2H, J = 7.6 Hz), 4.05 (t, 4H, J = 7.2 Hz) and 6.19 (s, 1H); 13C NMR (CDCl3) delta 16.2, 23.9, 50.1, 109.1, 163.2 and 167.0; mass spectrum (FAB), m/z 164.1192 (M+H)+ (C9H14N3 requires m/z 164.1188).
65%	With copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 4h;	To a stirred solution containing 655 mg (6.99 mmol) of azetidine hydrochloride, 133 mg (6.99 mmol) of Cul, and 3.42 g (10.5 mmol) of Cs2CO3 in 10 mL dry degassed DMF was added 500 mg (3.49 mmol) of <strong>[4472-44-0]2-chloro-4,6-dimethylpyrimidine</strong> and 165 mg (6.99 mmol) 3,4,7,8-tetramethyl- 1,1 0-phenanthroline sequentially. The reaction mixture was stirred at 50 °C for 4 h. The reaction mixture was allowed to warm to room temperature and was then filtered through Celite, and the Celite pad was washed with CH2C12. The combined organic phase was washed with water and then with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (15 x 3 cm). Elution with hexane followed by 4:1 hexane?EtOAc and then 1:1 hexane?EtOAc afforded 43 as yellowish solid: yield 372 mg (65percent); mp 5 1-52 °C; silica gel TLC Rf 0.22 (3:2 hexane?EtOAc); ?H NMR (CDCI3, 400 MHz) 2.20 (s, 6H),2.24 (t, 2H, J= 7.6 Hz), 4.05 (t, 4H, J? 7.2 Hz) and 6.19 (s, 1H); ?3C NMR (CDC13, 100 MHz) oe16.2, 23.9, 50.1, 109.1, 163.2 and 167.0; mass spectrum (FAB), m/z 164.1192 (M+H) (C9H14N3 requires 164.1188).

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5206 - 5220
[2]Patent: WO2016/133959,2016,A1 .Location in patent: Page/Page column 50

20
[ 199177-26-9 ]
[ 78797-58-7 ]
3-[(1-azetidinyl)methyl]-5-bromophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With ethanol; sodium tris(acetoxy)borohydride; at 20℃; for 12h;	Sodium triacetoxy borohydride (1.6 g, 7.5 mmol) was added to a stirring mixture of 3-bromo-5- hydroxy benzaldehyde (1 g, 5 mmol) and azetidine hydrochloride (0.58 g, 9.9 mmol) in ethanol 30 mL) at ambient temperature for 12 hours. The mixture was diluted with DI water, concentrated and purified by reversed phase HPLC (5-95% acetonitrile in DI water containing 0.1% formic acid: 20 minute gradient). The pure fractions were pooled and lyophilized to afford the product as a clear viscous oil. Yield 78 %.1H- NMR (300 MHz, MeOD d4) delta 8.55 (s, 1H), 7.10, s, 1H), 7.03 (s, 1H), 6.88 (s, 1H), 4.24 (s, 2H), 4.12 (t, 4H, J=8.1 Hz), 2.54 (m, 2H, J=8.1 Hz).

Reference： [1]Patent: WO2016/201219,2016,A1 .Location in patent: Page/Page column 70-71

21
[ 1331742-86-9 ]
[ 78797-58-7 ]
C₁₀H₈N₄S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8842 - 8847

22
[ 3883-95-2 ]
[ 78797-58-7 ]
2-(azetidine-1-carbonyl)-6-bromophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95 mg	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 1h;	to the DMF solution (5 mL) of <strong>[3883-95-2]3-bromo-2-hydroxybenzonic acid</strong> (1.0 mmol, 217 mg) was added triethyl amine (3.0 eq., 3.0 mmol, 0.415 mL), HATU (1.5 eq., 1.5 mmol, 570 mg) and the HCl salt of azetidine (1.5 eq., 1.5 mmol, 141 mg). The resulting mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine. The organic layer was separated, dried with Na2SO4 and concentrated. The residue obtained was purified by silica gel chromatography eluting with ethyl acetate/hexane (0?50%) to give 95 mg of the desired product as a yellow foam. MS (M+H)+=631.5.

Reference： [1]Patent: US2018/16252,2018,A1 .Location in patent: Paragraph 1194

23
[ 36404-88-3 ]
[ 78797-58-7 ]
2-(azetidin-1-yl)nicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 20h;	Into a 40 mL vial was added azetidine hydrochloride (0.412 g, 4.40 mmol), 2-chloronicotinaldehyde (0.53 g, 3.67 mmol), K2CO3 (1.268 g, 9.17 mmol) and dimethyl sulfoxide (DMSO) (7.34 mL). The mixture was stirred at 110 C. for 20 hours. Saturated ammonium chloride was added, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash column chromatography (0 to 30% ethyl acetate in heptane) to provide 2-(azetidin-1-yl)nicotinaldehyde (0.52 g, 3.21 mmol, 87% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 9.86 (s, 1H), 8.29 (dd, J=4.6, 1.9 Hz, 1H), 7.96 (dd, J=7.6, 1.9 Hz, 1H), 6.75 (dd, J=7.6, 4.6 Hz, 1H), 4.09 (d, J=15.2 Hz, 3H), 3.29 (s, 2H), 2.37-2.24 (m, 3H); MS (ESI+) m/z 163.0 (M+H)+.

Reference： [1]Patent: US2018/99931,2018,A1 .Location in patent: Paragraph 2100

24
[ 1448307-66-1 ]
[ 78797-58-7 ]
4-[(1-azetidinyl)methyl]-1-(2-chloro-4-pyrimidinyl)-3-methyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In dichloromethane; at 20.0℃;	A stirred suspension of l-(2-chloro-4-pyrimidinyl)-3-methyl-lH-pyrazole-4- carbaldehyde (444 mg, 2.0 mmol) and 3-azetidine hydrochloride (374 mg, 4.0 mmol) in dichloromethane (25 mL) was treated with portionwise addition of Na(OAc)3BH (848 mg, 4.0 mmol). The resulting mixture was stirred at room temperature overnight. Next morning, LCMS analysis indicated clean conversion to product. The reaction was quenched by addition of H20 (20 mL) and IN NaOH aqueous solution (20 mL). This was transferred to a separatory funnel, the organic layer was separated, dried over anhydrous MgS04, filtered and concentrated in vacuo. The crude product was obtained as a light yellow solid (556 mg, > 2.0 mmol, -quant.). LC/MS - HPLC (254 nm) - Rt 0.03 min. MS (ESI) m/z 264.1 [M+ + H+]. Purity = 85 % by UV (254 nm).

Reference： [1]Patent: WO2018/226739,2018,A1 .Location in patent: Paragraph 0239

25
[ 3430-26-0 ]
[ 78797-58-7 ]
2-(azetidin-1-yl)-5-bromo-4-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With caesium carbonate; In dimethyl sulfoxide; at 90℃; for 20h;	Cs2C03 ( 3.4 g, 10.526 mmol) was added to a stirred solution of <strong>[3430-26-0]2,5-dibromo-4-methylpyridine</strong> (1.0 g, 5.263 mmol) and azetidine hydrochloride (0.5 g, 5.263 mmol) in DMSO (10 mL) at RT. The resulting reaction mixture was heated to 90C and maintained under stirring for 20 h. The reaction completion was monitored by TLC To the reaction mixture, water (30 mL) was added and extracted with ethyl acetate (2 x 30 mL). The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 0.8 g (66%) of 2-(azetidin-l-yl)-5-bromo-4-methylpyridine as a pale yellow solid. (TLC system: 30%o ethyl acetate in pet-ether; Rf: 0.7).

Reference： [1]Patent: WO2019/12037,2019,A1 .Location in patent: Paragraph 0208; 0209; 0210

26
[ 882672-05-1 ]
[ 78797-58-7 ]
2-(azetidin-1-yl)-6-bromoquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With triethylamine; In 1,4-dioxane; at 120℃; for 0.666667h;Microwave irradiation;	6 -Bromo-2-chloroquinazoline (300 mg, 1.2 mmol), azetidine HC1 salt (173 mg, 1.85 mmol), triethylamine (1.72 mL, 12.3 mmol) and l,4-dioxane (10 mL) were added to the 25 mL microwave vial. The reaction mixture was heated in microwave reactor at l20C for 40 minutes. By LCMS targeted molecule was formed while some unreacted starting material was still remaining (the ratio between targeted molecule and starting material is about 2: 1 by LCMS). The reaction mixture was concentrated and purified on silica using ethyl acetate and hexanes. 2-(Azetidin-l-yl)-6-bromoquinazoline was obtained in 14% yield. 1H NMR (400 MHz, Chloroform-d): d 8.87 (s, 1H), 7.75 (d, J= 2.3 Hz, 1H), 7.67 (dd, J= 9.1, 2.3 Hz, 1H), 7.44 (d, J= 9.0 Hz, 1H), 4.24 (t, J= 7.5 Hz, 4H), 2.40 (p, J= 7.5 Hz, 2H) ppm.

Reference： [1]Patent: WO2019/236631,2019,A1 .Location in patent: Paragraph 0542

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[ CAS No. 78797-58-7 ] {[proInfo.proName]}

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[ 78797-58-7 ] Synthesis Path-Upstream 1~1

[ 78797-58-7 ] Synthesis Path-Downstream 1~26

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