[ CAS No. 1420271-08-4 ]

Name: 1420271-08-4|2-Azaspiro[3.3]heptane hydrochloride|98%
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Quality Control of [ 1420271-08-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1420271-08-4 ]

CAS No. :	1420271-08-4	MDL No. :	MFCD21607345
Formula :	C₆H₁₂ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	133.62 g/mol	Pubchem ID :	71741940
Synonyms :

Calculated chemistry of of [ 1420271-08-4 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.15
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.52
Log Po/w (WLOGP) :	1.18
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	1.23

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.63
Solubility :	3.16 mg/ml ; 0.0237 mol/l
Class :	Very soluble
Log S (Ali) :	-1.38
Solubility :	5.56 mg/ml ; 0.0416 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.5
Solubility :	4.26 mg/ml ; 0.0319 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 1420271-08-4 ]

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

Application In Synthesis of [ 1420271-08-4 ]

* 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 [ 1420271-08-4 ]
Downstream synthetic route of [ 1420271-08-4 ]

[ 1420271-08-4 ] Synthesis Path-Upstream 1~3

1
[ 5445-51-2 ]
[ 1420271-08-4 ]

Reference： [1] Patent: CN103635456, 2016, B,

2
[ 4415-73-0 ]
[ 1420271-08-4 ]

Reference： [1] Patent: CN103635456, 2016, B,

3
[ 64936-58-9 ]
[ 1420271-08-4 ]

Reference： [1] Patent: CN103635456, 2016, B,

[ 1420271-08-4 ] Synthesis Path-Downstream 1~17

1
[ 488818-70-8 ]
[ 1420271-08-4 ]
[ 1420294-44-5 ]

Yield	Reaction Conditions	Operation in experiment
60 mg		Compound A (0.230g, 0.474mmol) was dissolved in DMF (2mmol), and added <strong>[1420271-08-4]2-azaspiro[3.3]heptane hydrochloride</strong> (0.126g, 0.948mmol) and triethylamine (180mg, 1.8mmol). After the mixture was stirred at room temperature for 30 minutes, added sodium cyanoborohydride (0.2g, 1.7mmol), then stirred for 4 hours at room temperature, separated by HPLC to give Compound 9 (60mg). 1H-NMR (CD3OD, 400 MHz) δ : 7.57 (s, 1H), 4.35 (br. s., 2H), 4.16 (br. s., 4H), 3.69 (s, 1H), 3.34 - 3.50 (m, 1H), 2.82 - 2.97 (m, 7H), 2.77 (d, 1H), 2.56 - 2.70 (m, 6H), 2.29 (t, 4H), 2.20 (d, 2H), 1.85 (m, 2H), 1.57 - 1.71 (m,1H)

Reference： [1]Patent: EP2738156,2014,A1 .Location in patent: Paragraph 0137-0138

2
[ 1420271-08-4 ]
(4S,4aS,5aR,12aS)-9-(2-azaspiro[3.3]heptan-2-ylmethyl)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,1'-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; triethylamine; In N,N-dimethyl-formamide;	Example 8 Preparation of (4S,4aS,5aR,12aS)-9-(2-azaspiro[3.3]heptan-2-ylmethyl)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,1'-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (Compound 9) Compound A (0.230 g, 0.474 mmol) was dissolved in DMF (2 mmol), and added <strong>[1420271-08-4]2-azaspiro[3.3]heptane hydrochloride</strong> (0.126 g, 0.948 mmol) and triethylamine (180 mg, 1.8 mmol). After the mixture was stirred at room temperature for 30 minutes, added sodium cyanoborohydride (0.2 g, 1.7 mmol), then stirred for 4 hours at room temperature, separated by HPLC to give Compound 9 (60 mg). 1H-NMR (CD3OD, 400 MHz) δ: 7.57 (s, 1H), 4.35 (br. s., 2H), 4.16 (br. s., 4H), 3.69 (s, 1H), 3.34-3.50 (m, 1H), 2.82-2.97 (m, 7H), 2.77 (d, 1H), 2.56-2.70 (m, 6H), 2.29 (t, 4H), 2.20 (d, 2H), 1.85 (m, 2H), 1.57-1.71 (m, 1H)

Reference： [1]Patent: US2014/179638,2014,A1 .Location in patent: Page/Page column

3
[ 1420271-08-4 ]
1-(3,5-dibromo-1H-1,2,4-triazol-1-yl)-2-methylpropan-2-ol [ No CAS ]
1-(3-bromo-5-(2-azaspiro[3.3]heptan-2-yl)-1H-1,2,4-triazol-1-yl)-2-methylpropan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl acetamide; at 120℃;	Intermediate 12 l-(3-Bromo-5-(2-azaspiro[3.3]heptan-2-yl)-lH-l,2,4-triazol-l-yl)-2-methylpropan-2-ol l-(3,5-Dibromo-lH-l,2,4-triazol-l-yl)-2-methylpropan-2-ol (121 mg, 0.40 mmol) and 2- azaspiro[3.3]heptane hydrochloride (108 mg, 0.81 mmol) were mixed in dioxane (2 mL) and DMA (0.1 mL). N,N-Diisopropylethylamine (0.282 mL, 1.62 mmol) was added and the mixture was heated at 120C overnight. The solvents were evaporated and the residue was purified by column chromatography on silica gel eluting with a gradient of methanol in DCM yielding the title compound as a dry film (100 mg, 78 %). MS (ESI+) m/z 315 (M+H)+. XH NMR (500 MHz, CDCI3) δ 1.22 (s, 3 H), 1.28 (s, 3 H), 1.67 - 1.78 (m, 1 H), 1.78 - 2.00 (m, 3 H), 2.22 (t, 2 H), 3.50 - 3.71 (m, 1 H), 3.77 (s, 1 H), 3.97 - 4.20 (m, 3 H).

Reference： [1]Patent: WO2014/195321,2014,A1 .Location in patent: Page/Page column 20

4
[ 1420271-08-4 ]
(±)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide [ No CAS ]
(±)-1-[4-(2-azaspiro[3.3]hept-2-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzo-diazepine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2%	With tris(dibenzylideneacetone)dipalladium (0); sodium t-butanolate; DavePhos; In tetrahydrofuran; at 85℃; for 0.5h;Inert atmosphere;	Example 37 (±)-1-[4-(2-Azaspiro[3.3]hept-2-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (0886) (0887) Under argon, 100 mg (231 μmol) of (±)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 30A), 6.4 mg (7 μmol) of tris(dibenzylideneacetone)dipalladium (CAS [51364-51-3]) and 9.2 mg (23 mol) of 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos, CAS [213697-53-1]) were initially charged in 2.5 ml of degassed THF in a microwave glass, and the mixture was degassed carefully by introduction of argon. Under argon countercurrent, 31 mg (0.32 mmol) of sodium tert-butoxide and then 124 mg (0.925 mmol) of <strong>[1420271-08-4]2-azaspiro[3.3]heptane hydrochloride</strong> (1:1) (CAS[1420271-08-4]) were added. The mixture was degassed again and saturated with argon, the vessel was closed and the mixture was stirred at 85 C. for 30 minutes. After cooling, the mixture was partitioned between water and ethyl acetate and the phases were separated. The solvents were removed on a rotary evaporator and the residue was purified by preparative RP-HPLC. This gave 2.1 mg (2% of theory) of the desired product. (0888) LCMS (method 2): Rt=1.35 min; m/z=449.8 (M+H)+ (0889) 1H-NMR (300 MHz, CDCl3): δ=1.17 (d, 3H), 1.48-1.98 (m, 2H), 2.25 (t, 4H), 2.71 (dd, 1H), 2.87 (d, 3H), 2.92 (m, 1H), 3.73 (s, 3H), 3.93 (s, 4H), 3.96 (s, 3H), 5.18-5.31 (m, 1H), 5.92-6.00 (m, 1H), 6.43 (d, 2H), 6.65 (s, 1H), 6.78 (s, 1H), 7.49 (d, 2H).
2%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In tetrahydrofuran; at 85℃; for 0.5h;Inert atmosphere;	Under argon, (+/-)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 30A), 100 mg (231 μmol), tris (dibenzylideneacetone) dipalladium (CAS [51364-51-3]) 6.4 mg (7 μmol) and 2 '- (dicyclohexylphosphino) - N, N- dimethylbiphenyl-2-amine (DavePhos, CAS [213697-53-1]) 9.2 mg (23 μmol) for the first time into the filled in 2.5 ml of THF degassed in a glass microwave, the mixture was carefully degassed by introduction of argon. Under argon counter-current, sodium tert-butoxide and 31 mg (0.32 mmol), followed by 2-azaspiro [3.3] heptane hydrochloride (1:1) (CAS [1420271-08-4]) 124 mg (0.925 mmol) was added to It was. The mixture was again degassed and saturated with argon and close the container, the mixture is stirred for 30 minutes at 85 . After cooling, the mixture was partitioned between water and ethyl acetate, and the phases separated. The solvent was removed by rotary evaporator and the residue was purified by year for refining RPHPLC. In this manner, to give the desired product 2.1 mg (2% of theory).

Reference： [1]Patent: US2016/129011,2016,A1 .Location in patent: Paragraph 0886; 0887; 0888; 0889
[2]Patent: KR2015/119926,2015,A .Location in patent: Paragraph 1070-1074

5
[ 1420271-08-4 ]
[ 121-51-7 ]
2-[(3-nitrophenyl)sulfonyl]-2-azaspiro[3.3]heptane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
310 mg	With triethylamine; In dichloromethane; at 0℃; for 18h;	At a bath temperature of 0C, to 0.27g 3-nitrobenzenesulfonyl chloride (CAS121-51-7) and 0.17g <strong>[1420271-08-4]2-azaspiro[3.3]heptane hydrochloride</strong> (1: 1) (CAS665-04-3) added in 27ml methylene chloride, 0.65ml triethylamine, and stirred for 18 hours, during this process slowly increasing the temperature to room temperature. The reaction mixture was diluted with dichloromethane and washed with water and saturated sodium chloride solution, with sodium sulfate and completely concentrated under vacuum. To give 310mg 2-[(3-nitrophenyl)sulfonyl]-2-azaspiro[3.3]heptane.

Reference： [1]Patent: CN105518001,2016,A .Location in patent: Paragraph 0440

6
[ 5445-51-2 ]
[ 1420271-08-4 ]

Reference： [1]Patent: CN103635456,2016,B

7
[ 4415-73-0 ]
[ 1420271-08-4 ]

Reference： [1]Patent: CN103635456,2016,B

8
[ 64936-58-9 ]
[ 1420271-08-4 ]

Reference： [1]Patent: CN103635456,2016,B

9
2-p-toluenesulfonyl-2-azaspiro[3.3]heptane [ No CAS ]
[ 1420271-08-4 ]

Yield	Reaction Conditions	Operation in experiment
47.6%	With sodium; In pentan-1-ol; at 110℃; for 1h;	The 8-4 (6.4g, 25.4mmol) was dissolved in 100mL of n-pentanol, 5.3g sodium metal pieces into the wherein, after the reaction at 110 refluxed one hour, cooled, poured into 100mL water, divided night, the organic phase washed with 2N hydrochloric acid, water and concentrated Xiangde 8-5 (1.6g), a yield of 47.6%.

Reference： [1]Patent: CN103635456,2016,B .Location in patent: Paragraph 0243-0245

10
[ 1420271-08-4 ]
[ 156263-30-8 ]
(4S,4aS,5aR,12aS)-9-(2-(2-azaspiro[3.3]hexan-2-yl)acetamido)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23mg	With triethylamine; In acetonitrile; at 20℃; for 1h;	The 8-6 (400mg, 0.7mmol) and 8-5 (200mg, 1.5mmol) was dissolved in 5mL of acetonitrile was added 0.5mL TEA, the reaction at room temperature for 1 hour, after completion of 23mg Compound 8 was separated by HPLC.

Reference： [1]Patent: CN103635456,2016,B .Location in patent: Paragraph 0233; 0249-0253

11
[ 1420271-08-4 ]
5-chloro-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4-yl]methyl]pyridazin-3-one [ No CAS ]
5-(2-azaspiro[3.3]heptan-2-yl)-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4-yl]methyl]pyridazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In dimethyl sulfoxide; acetonitrile; at 70℃; for 18h;	General procedure: To a stirred suspension of 5-chloro-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4- yl]methyl]pyridazin-3-one (building block A, 300 mg, 0.947 mmol) and (R)-3- hydroxypyrrolidine (0.14 mL, 1.73 mmol) in DMSO (0.5 mL) and acetonitrile (3 mL) was added potassium carbonate (393 mg, 2.84 mmol) Then the reaction mixture was stirred at 70 C for 18 h. After cooling to room temperature the reaction mixture was diluted with EtOAc (80 mL) was washed three times with water (10 mL) and brine (10 mL). The aqueous layers were back extracted twice with EtOAc (80 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated in vacuo. Purification by flash chromatography (silica, gradient: 0% to 10% MeOH in CH2CI2) afforded the title compound (341 mg, 93 %) as an off-white foam. MS (ESI): 368.2 ([M+H]+).

Reference： [1]Patent: WO2019/238633,2019,A1 .Location in patent: Page/Page column 142; 171

12
[ 1420271-08-4 ]
N-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]methyl}-1-[(6-fluoro-2-methylpyridin-3-yl)methyl]-1H-pyrazole-4-carboxamide [ No CAS ]
1-[(6-{2-azaspiro[3.3]heptan-2-yl}-2-methylpyridin-3-yl)methyl]-N-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]methyl}-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 168h;	N-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]methyl}-1-[(6-fluoro-2-methylpyridin-3-yl)methyl]-1 H-pyrazole-4- carboxamide (43 mg) dissolved in DMSO (1 mL), <strong>[1420271-08-4]2-azaspiro[3.3]heptane hydrochloride</strong> (20 mg) and N,N-diisopropylethylamine (50 mL) are added and the mixture is stirred for 7 d at 60C and the mixture is purified by HPLC on reversed phase (ACN, water) to give the title compound.LC (Method 1): tR= 0.83 min; Mass spectrum (ESI+): m/z = 504 [M+H]+.

Reference： [1]Patent: WO2020/74442,2020,A1 .Location in patent: Page/Page column 90; 91

13
[ 1420271-08-4 ]
ethyl 4-methyl-2-(2-oxo-5-(2-oxoethyl)-4-(trifluoromethyl)pyridin-1(2H)-yl)pentanoate [ No CAS ]
ethyl 2-(5-(2-(2-azaspiro[3.3]heptan-2-yl)ethyl)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl)-4-methylpentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of ethyl 2-(2-oxo-5-(2-oxoethyl)-4-(trifluoromyl)pentanoate (750 mg, 2.25 mmol) in DCE (10 mL) at 25 C was added dimethylamine (2M in THF, 1.7 mL, 3.4 mmol) and stirred at 25 C for 10 min. NaBH(OAc)3(950 mg, 4.5 mmol) was added and stirred at 25 C for 2 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel column (DCM: MeOH 10:1) to provide ethyl 2-(5-(2- (dimethylamino)ethyl)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl)pentanoate as a yellow oil (630 mg). Yield 77% (ESI 363.1 (M+H)+).

Reference： [1]Patent: WO2021/76890,2021,A1 .Location in patent: Page/Page column 239; 316

14
[ 75-15-0 ]
tauredon [ No CAS ]
[ 1420271-08-4 ]
C₁₄H₂₀Au₂N₂S₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2021,vol. 27,p. 12156 - 12165

15
N-Boc-2-azaspiro[3,3]heptane [ No CAS ]
[ 1420271-08-4 ]

Yield	Reaction Conditions	Operation in experiment
2.6 g	With hydrogenchloride; In ethyl acetate; at 20℃; for 0.5h;	The aqueous solution of 2-azaspiro[3.3]heptane was adjusted to pH 9-10 with sodium hydroxide, and 50 mL of tetrahydrofuran and 4.6 g of Boc2O were added. After stirring at room temperature for 5 hours, the reaction solution was extracted 3 times with ethyl acetate. The extracts were combined and dried by adding anhydrous sodium sulfate. After filtration, the filtrate was concentrated and passed through a column to obtain 4.3 g of Boc-2-azaspiro[3.3]heptane. 4.3 g of Boc-2-azaspiro[3.3]heptane was dissolved in 20 mL of ethyl acetate, and 10 mL of 6N hydrochloric acid gas/ethyl acetate solution was added. The reaction was stirred at room temperature for 30 minutes, the solution was spin-dried, and the solvent was taken twice with dichloromethane to obtain 2.6 g of 2-azaspiro[3.3]heptane hydrochloride.

Reference： [1]Patent: CN112920103,2021,A .Location in patent: Paragraph 0006-0007; 0012

16
[ 1420271-08-4 ]
2-(6-cyano-1H-indol-2-yl)ethyl 4-methylbenzene-1-sulfonate [ No CAS ]
2-[2-(2-azaspiro[3.3]heptanean-2-yl)ethyl]-1H-indole-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With N-ethyl-N,N-diisopropylamine; sodium iodide; In dimethyl sulfoxide; at 50℃; for 3h;	2-(6-cyano-1H-indol-2-yl)ethyl 4-methylbenzenesulfonate (300 mg, 0.881 mmol), <strong>[1420271-08-4]2-azaspiro[3.3]heptane hydrochloride</strong> (0.37 mL, 1.32 mmol), sodium iodide (16 mg, 0.110 mmol) and N-ethyl-N-(propan-2-yl)propan-2-amine (0.31 mL, 1.76 mmol) were combined in DMSO (6.6 mL) and the mixture was stirred at 50C for 3 h. The mixture was cooled to room temperature, diluted with EtOAc (20 mL) and washed with NaHCO3 (sat., 20 mL). A white insoluble solid was removed by filtration, the layers were separated, and the mixture was extracted with EtOAc (3x20 mL). The organics were washed with brine (50 mL), dried over MgSO4, and concentrated under vacuum to a residue which was purified by chromatography on SiO2 (eluting with 0-100% EtOAc/heptane then 0-20% MeOH/ EtOAc) to give the title compound (62 mg,19%) as an orange oil. Method A: LC-MS (electrospray): m/z = 266.3 (M+H)+, RT = 0.86 min

Reference： [1]Patent: WO2021/111124,2021,A1 .Location in patent: Page/Page column 311

17
[ 1420271-08-4 ]
9-(2-benzyl-6-chloro-3-oxo-2,3-dihydropyridazin-4-yl)-1-(3,4-difluorophenyl)-1,9-diazaspiro[5.5]undecane-2-one [ No CAS ]
9-(2-benzyl-3-oxo-6-(2-azaspiro[3.3]heptan-2-yl)-(2,3-dihydropyridazin-4-yl))-1-(3,4-difluorophenyl)-1,9-diazaspiro[5.5]undecane-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.068 g	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; johnphos; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere;	A solution of 9-(2-benzyl-6-chloro-3-oxo-2,3-dihydropyridazin-4-yl)-1-(3,4- difluorophenyl)-1,9-diazaspiro[5.5]undecane-2-one (0.100 g, 0.200 mmol) and 2- azaspiro[3.3]heptane hydrochloride (0.053 g, 0.40 mmol) in dioxane (6 mL) was stirred with argon purging for ten minutes. Cs2CO3 (0.195 g, 0.600 mmol) was added to the reaction mixture under argon purging followed by the addition of Pd2(dba)3 (30 mg, 0.040 mmol) and JohnPhos (10 mg, 0.040 mmol). The mixture was heated at 100C for 16 h. After cooling to RT, water was added to the reaction mixture and it was extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (60-70% EtOAc:hexane) provided the title compound as a white solid (0.068 g, 0.12 mmol).1H NMR (400 MHz, chloroform-d) δ 7.46 - 7.34 (m, 2H), 7.24 - 7.09 (m, 2H), 6.95 - 6.82 (m, 1H), 6.82 - 6.69 (m, 1H), 5.64 (s, 1H), 5.09 (s, 2H), 3.9 - 4.05 (m, 3H), 3.8 (s, 3H), 2.65 - 2.75 (m, 2H), 2.58 - 2.61 (m, 2H), 2.14 (t, 3H), 1.98 - 2.12 (m, 4H), 1.8 - 1.92 (m, 4H), 1.7 - 1.78 (m, 3H); m/z = 560.3 [M+H]+; tR = 1.64 min (LCMS method j)
0.068 g	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; johnphos; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere;	A solution of 9-(2-benzyl-6-chloro-3-oxo-2,3-dihydropyridazin-4-yl)-1-(3,4- difluorophenyl)-1,9-diazaspiro[5.5]undecane-2-one (0.100 g, 0.200 mmol) and 2- azaspiro[3.3]heptane hydrochloride (0.053 g, 0.40 mmol) in dioxane (6 mL) was stirred with argon purging for ten minutes. Cs2CO3 (0.195 g, 0.600 mmol) was added to the reaction mixture under argon purging followed by the addition of Pd2(dba)3 (30 mg, 0.040 mmol) and JohnPhos (10 mg, 0.040 mmol). The mixture was heated at 100C for 16 h. After cooling to RT, water was added to the reaction mixture and it was extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (60-70% EtOAc:hexane) provided the title compound as a white solid (0.068 g, 0.12 mmol).1H NMR (400 MHz, chloroform-d) δ 7.46 - 7.34 (m, 2H), 7.24 - 7.09 (m, 2H), 6.95 - 6.82 (m, 1H), 6.82 - 6.69 (m, 1H), 5.64 (s, 1H), 5.09 (s, 2H), 3.9 - 4.05 (m, 3H), 3.8 (s, 3H), 2.65 - 2.75 (m, 2H), 2.58 - 2.61 (m, 2H), 2.14 (t, 3H), 1.98 - 2.12 (m, 4H), 1.8 - 1.92 (m, 4H), 1.7 - 1.78 (m, 3H); m/z = 560.3 [M+H]+; tR = 1.64 min (LCMS method j)

Reference： [1]Patent: WO2022/34529,2022,A1 .Location in patent: Page/Page column 98-99
[2]Patent: WO2022/34529,2022,A1 .Location in patent: Page/Page column 98-99

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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

[ CAS No. 1420271-08-4 ]

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[ 1420271-08-4 ] Synthesis Path-Upstream 1~3

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Aliphatic Heterocycles

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