1240584-34-2|(R)-tert-Butyl 3-phenylpiperazine-1-carboxylate| Ambeed

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Quality Control of [ 1240584-34-2 ] Purity: 95% SDS Specification

COA

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NMR

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Product Details of [ 1240584-34-2 ]

CAS No. :	1240584-34-2
Formula :	C₁₅H₂₂N₂O₂
M.W :	262.35
SMILES Code :	O=C(N1C[C@@H](C2=CC=CC=C2)NCC1)OC(C)(C)C
MDL No. :	MFCD08685942
InChI Key :	HRRFJZULVYGVNJ-ZDUSSCGKSA-N
Pubchem ID :	7015616

Safety of [ 1240584-34-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1240584-34-2 ]

* 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 [ 1240584-34-2 ]

[ 1240584-34-2 ] Synthesis Path-Downstream 1~37

1
[ 1036403-32-3 ]
[ 1240584-34-2 ]
C₃₀H₃₄FN₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	General procedure: To a solution of compound 19 (100 mg, 0.33 mmol) in anhydrous DMF (3 mL) was added appropriate amine (0.43 mmol), EDC (82 mg, 0.43 mmol), 1-hydroxybenzotriazole monohydrate (66 mg, 0.43 mmol), and triethylamine (43 mg, 0.43 mmol). The reaction mixture was stirred at rt overnight, and partitioned between methylene chloride and brine. The organic phase was washed with brine, water, and concentrated. The residue was separated by HPLC to provide compounds 20. For compounds 20f, 20g, and 20h whose syntheses involved the use of BOC-protected amine, the coupling product was then treated with TFA (0.5 ml) in CH2Cl2 (2 mL) at rt for 1 h. Removal of the volatiles provided the crude 20 that can be further purified by HPLC to give the title products.

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4635 - 4645.

2
[ 1036403-32-3 ]
[ 1240584-34-2 ]
[ 1073657-18-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4635 - 4645.

3
[ 1399859-54-1 ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

4
[ 1399859-44-9 ]
[ 1240584-34-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 20% Pd(OH)2/C; hydrogen; In ethanol; at 20℃; for 18h;	General procedure: 20% Pd(OH)2 (0.052 mol) was added to a solution of 7a-c or 7′a (0.26 mmol) in EtOH (10 ml). The reaction was stirred under a H2-atmosphere at room temperature for 18 h and was then filtered through Celite. After concentration under reduced pressure, the crude product was diluted with H2O (10 mL) and extracted with EtOAc (3 × 10 mL). The combined organic fractions were washed with 1 N HCl (3 × 5 mL). The aqueous acid fractions were basified to pH 8-9 by the addition of NaHCO3 sat. while maintaining vigorous stirring. The aqueous mixture was extracted with EtOAc (3 × 10 mL). The combined organic fractions were washed with brine (10 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to give the enantiomerically pure N-Boc-piperazines.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

5
[ 1399859-55-2 ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

6
[ 1399859-56-3 ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

7
[ 70-11-1 ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

8
N-(2-oxo-2-phenylethyl)glycine methyl ester [ No CAS ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

9
[ 24424-99-5 ]
C₁₈H₂₂N₂O [ No CAS ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

10
[ 1399859-50-7 ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

11
C₂₅H₂₆N₂O₂ [ No CAS ]
[ 1240584-34-2 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5215 - 5218.

12
[ 32315-10-9 ]
[ 1240584-34-2 ]
tert-butyl (R)-4-(chlorocarbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 1.5h;	General procedure: To a solution of the appropriate amine (1 equiv.) and pyridine or DIPEA (2-5 equiv.) in DCM or THF at 0 C was added a solution of triphosgene (0.3-0.6 equiv.) in DCM or THF, respectively, at 0 C. The reaction was allowed to warm to rt and stirred for 1-24 h before being quenched with 0.5-1 M HCI and extracted with DCM (x 3) using a phase separator.The combined organic phases were concentrated in vacuo to give the product that was used in the next step without further purification.
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 1.5h;	General procedure: To a solution of the appropriate amine (1 equiv.) and pyridine or DI PEA (2-5 equiv.) in DCM or THF at 0 C was added a solution of triphosgene (0.3-0.6 equiv.) in DCM or THF, respectively, at 0 C. The reaction was allowed to warm to rt and stirred for 1-24 h before being quenched with 0.5-1 M HCI and extracted with DCM (x 3) using a phase separator. (0747) The combined organic phases were concentrated in vacuo to give the product that was used in the next step without further purification.

References: [1]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 91; 164.
[2]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 71-72; 144-145.

13
[ 32315-10-9 ]
[ 1240584-34-2 ]
1-((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-5-methylpyrazin-2(1H)-one [ No CAS ]
tert-butyl (3R)-4-(10-hydroxy-10-((5-methyl-2-oxopyrazin-1(2H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		To a solution triphosgene (5.4 mg, 0.0180 mmol) in MeCN (0.36 ml_) at 0 C was added pyridine (17 pl_, 0.210 mmol). After 20 min, a solution of te/f-butyl ( )-3-phenylpiperazine-1-carboxylate (14.2 mg, 0.0541 mmol) in MeCN (0.36 ml_) was added and the reaction mixture was stirred at 0 C for a further 15 min before being allowed to warm to rt. After stirring for 2 h, 1 -((10- hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-5-methylpyrazin-2(1 /-/)-one (10 mg, 0.0361 mmol) and DIPEA (32 mI_, 0.180 mmol) were added. The reaction was stirred at rt for 2 h 30 min before saturated NaHC03(aq) (15 ml_) was added and the resulting mixture was extracted with DCM (3 x 10 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give title compound (17.5 mg, 85%) as an off-white foam. LCMS (Method A): RT = 1.42 min, m/z = 566 [M+H]+.
85%		To a solution triphosgene (5.4 mg, 0.0180 mmol) in MeCN (0.36 rriL) at 0 C was added pyridine (17 pL, 0.210 mmol). After 20 min, a solution of ferf-butyl (R)-3-phenylpiperazine-1-carboxylate (14.2 mg, 0.0541 mmol) in MeCN (0.36 ml_) was added and the reaction mixture was stirred at 0 C for a further 15 min before being allowed to warm to rt. After stirring for 2 h, 1-((10- hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-5-methylpyrazin-2(1H)-one (10 mg, 0.0361 mmol) and DIPEA (32 pL, 0.180 mmol) were added. The reaction was stirred at rt for 2 h 30 min before saturated NaHC03(aq) (15 ml_) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give title compound (17.5 mg, 85%) as an off-white foam. LCMS (Method A): RT = 1.42 min, m/z = 566 [M+H]+.

References: [1]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 147.
[2]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 165; 166.

14
[ 32315-10-9 ]
[ 1240584-34-2 ]
1-((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-3-methylpyrazin-2(1H)-one [ No CAS ]
tert-butyl (3R)-4-(10-hydroxy-10-((3-methyl-2-oxopyrazin-1(2H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		To a solution of triphosgene (5.4 mg, 0.0180 mmol) in MeCN (0.36 mL) at 0 C was added pyridine (17 pL, 0.210 mmol). After 20 min, a solution of te/f-butyl ( )-3-phenylpiperazine-1-carboxylate (14.2 mg, 0.0541 mmol) in MeCN (0.36 mL) was added and the reaction mixture was stirred at 0 C for a further 15 min before being allowed to warm to rt. After stirring for 3 h, 1 -((10- hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-3-methylpyrazin-2(1/-/)-one (10 mg, 0.0361 mmol) and DIPEA (32 pL, 0.180 mmol) were added. The reaction was stirred at rt for 16 h before saturated NaHC03(aq) (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give title compound (15.7 g, 77%) as an off-white foam. LCMS (Method A): RT = 1.43 min, m/z = 566 [M+H]+.
77%		To a solution of triphosgene (5.4 mg, 0.0180 mmol) in MeCN (0.36 mL) at 0 C was added pyridine (17 pL, 0.210 mmol). After 20 min, a solution of tert- butyl (R)-3-phenylpiperazine-1-carboxylate (14.2 mg, 0.0541 mmol) in MeCN (0.36 mL) was added and the reaction mixture was stirred at 0 C for a further 15 min before being allowed to warm to rt. After stirring for 3 h, 1-((10- hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-3-methylpyrazin-2(1H)-one (10 mg, 0.0361 mmol) and DIPEA (32 pL, 0.180 mmol) were added. The reaction was stirred at rt for 16 h before saturated NaHCC>3(aq) (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give title compound (15.7 mg, 77%) as an off-white foam. LCMS (Method A): RT = 1.43 min, m/z = 566 [M+H]+.

References: [1]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 148-149.
[2]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 167; 168.

15
[ 32315-10-9 ]
[ 1240584-34-2 ]
(S)-1-((4-hydroxy-3,3-dimethylpiperidin-4-yl)methyl)-4-phenylpyridin-2(1H)-one [ No CAS ]
tert-butyl (R)-4-((S)-4-hydroxy-3,3-dimethyl-4-((2-oxo-4-phenylpyridin-1(2H)-yl)methyl)piperidine-1-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		A solution of triphosgene (9.5 mg, 0.0320 mmol) in THF (0.5 ml_) was added to a mixture of tert- butyl (R)- 3- phenylpiperazine-1-carboxylate (25.2 mg, 0.0960 mmol) and DIPEA (34 mI_, 0.192 mmol) in THF (0.5 ml_) at 0 C. After 10 min, the reaction mixture was allowed to warm to rt before being added via syringe to a solution of (S)-1-((4-hydroxy-3,3-dimethylpiperidin-4-yl)methyl)- 4-phenylpyridin-2(1 /-/)-one (20 mg, 0.0640 mmol) in DCM (0.64 ml_). The reaction was stirred at rt for 3 days before saturated NaHC03(aq) (15 ml_) was added and the resulting mixture was extracted with DCM (3 x 10 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane) to give the title compound (28 mg, 72%) as an off-white foam. LCMS (Method A): RT = 1.67 min, m/z = 601 [M+H]+.
72%		A solution of triphosgene (9.5 mg, 0.0320 mmol) in THF (0.5 ml_) was added to a mixture of tert- butyl (R)- 3- phenylpiperazine-1-carboxylate (25.2 mg, 0.0960 mmol) and DIPEA (34 pl_, 0.192 mmol) in THF (0.5 ml_) at 0 C. After 10 min, the reaction mixture was allowed to warm to rt before being added via syringe to a solution of (S)-1-((4-hydroxy-3,3-dimethylpiperidin-4-yl)methyl)- 4-phenylpyridin-2(1H)-one (20 mg, 0.0640 mmol) in DCM (0.64 ml_). The reaction was stirred at rt for 3 days before saturated NaHCO3(aq) (15 ml.) was added and the resulting mixture was extracted with DCM (3 x 10 ml.) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane) to give the title compound (28 mg, 72%) as an off-white foam. LCMS (Method A): RT = 1.67 min, m/z = 601 [M+H]+.

References: [1]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 246.
[2]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 265.

16
[ 32315-10-9 ]
[ 1240584-34-2 ]
(S)-1-((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-4-phenylpyridin-2(1H)-one [ No CAS ]
tert-butyl (R)-4-((S)-10-hydroxy-10-((2-oxo-4-phenylpyridin-1(2H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		A solution of triphosgene (21.9 mg, 0.0739 mmol) in THF (1.1 ml_) was added to a mixture of tert- butyl (R)- 3- phenylpiperazine-1-carboxylate (58.1 mg, 0.222 mmol) and DIPEA (77 mI_, 0.443 mmol) in THF (1.1 ml_) at 0 C. After 65 min, the reaction mixture was allowed to warm to rt before being added via syringe to a solution of (S)-1-((10-hydroxy-7-azaspiro[4.5]decan-10- yl)methyl)-4-phenylpyridin-2(1/-/)-one (50 mg, 0.148 mmol) in DCM (1.5 ml_). The reaction was stirred at rt for 17 h before saturated NaHC03(aq) (15 ml_) was added and the resulting mixture was extracted with DCM (3 x 10 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane) to give the title compound (71.2 mg, 76%) as an off-white foam. LCMS (Method A): RT = 1.75 min, m/z = 627 [M+H]+.
76%		A solution of triphosgene (21.9 mg, 0.0739 mmol) in THF (1.1 mL) was added to a mixture of tert-butyl (R)- 3- phenylpiperazine-1-carboxylate (58.1 mg, 0.222 mmol) and DIPEA (77 pL, 0.443 mmol) in THF (1.1 mL) at 0 C. After 65 min, the reaction mixture was allowed to warm to rt before being added via syringe to a solution of (S)-1-((10-hydroxy-7-azaspiro[4.5]decan-10- yl)methyl)-4-phenylpyridin-2(1H)-one (50 mg, 0.148 mmol) in DCM (1.5 mL). The reaction was stirred at rt for 17 h before saturated NaHCO3(aq) (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane) to give the title compound (71.2 mg, 76%) as an off-white foam. LCMS (Method A): RT = 1.75 min, m/z = 627 [M+H]+.

References: [1]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 245.
[2]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 263; 264.

17
[ 32315-10-9 ]
[ 1240584-34-2 ]
3-((5-hydroxy-9-oxa-2-azaspiro[5.5]undecan-5-yl)methyl)-6-phenylpyrimidin-4(3H)-one [ No CAS ]
tert-butyl (3R)-4-(5-hydroxy-5-((6-oxo-4-phenylpyrimidin-1(6H)-yl)methyl)-9-oxa-2-azaspiro[5.5]undecane-2-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		To a solution of triphosgene (12.5 mg, 0.0422 mmol) in THF (0.85 mL) at 0 C was added pyridine (34 pL, 0.422 mmol). After 30 min, a solution of te/f-butyl ( )-3-phenylpiperazine-1-carboxylate (33.2 mg, 0.127 mmol) in THF (0.85 mL) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After 2 h, 3-((5-hydroxy-9-oxa-2- azaspiro[5.5]undecan-5-yl)methyl)-6-phenylpyrimidin-4(3/-/)-one (30 mg, 0.0844 mmol) and DIPEA (44 pL, 0.253 mmol) were added. The reaction was stirred at rt for 16 h before saturated NaHC03(aq) (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give the title compound (45 mg, (1825) 82%) as a yellow solid. LCMS (Method A): RT = 1.51 min, m/z = 644 [M+H]+.
82%		To a solution of triphosgene (12.5 mg, 0.0422 mmol) in THF (0.85 mL) at 0 C was added pyridine (34 pL, 0.422 mmol). After 30 min, a solution of <strong>[1240584-34-2]tert-butyl (R)-3-phenylpiperazine-1-carboxylate</strong> (33.2 mg, 0.127 mmol) in THF (0.85 mL) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After 2 h, 3-((5-hydroxy-9-oxa-2- azaspiro[5.5]undecan-5-yl)methyl)-6-phenylpyrimidin-4(3H)-one (30 mg, 0.0844 mmol) and DIPEA (44 pL, 0.253 mmol) were added. The reaction was stirred at rt for 16 h before saturated NaHC03(aq> (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give the title compound (45 mg,82%) as a yellow solid. LCMS (Method A): RT = 1.51 min, m/z = 644 [M+H]+.

References: [1]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 275.
[2]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 293; 294.

18
[ 32315-10-9 ]
[ 1240584-34-2 ]
(S)-4-chloro-1-((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)pyridin-2(1H)-one hydrochloride [ No CAS ]
tert-butyl (R)-4-((S)-10-((4-chloro-2-oxopyridin-1(2H)-yl)methyl)-10-hydroxy-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		To a solution triphosgene (37.4 mg, 0.126 mmol) in DCM (2.5 mL) at 0 C was added pyridine (0.102 mL, 1.26 mmol). After 20 min, a solution of terf-butyl (R)-3-phenylpiperazine-1-carboxylate (99.2 mg, 0.378 mmol) in DCM (2.5 mL) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After 3 h, the reaction mixture was transferred via syringe to flask containing (S)-4-chloro-1-((10-hydroxy-7-azaspiro[4.5]decan- 10-yl)methyl)pyridin-2(1H)-one hydrochloride (84 mg, 0.252 mmol) before DIPEA (0.132 ml_, 0.756 mmol) was added. After stirring at rt for 4 days, the reaction had not reached full conversion so to a solution of triphosgene (18.7 mg, 0.063 mmol) in DCM (1.25 ml_) at 0 C in a separate flask was added pyridine (51 pl_, 0.630 mmol). After 20 min, a solution of tert- butyl (R)-3-phenylpiperazine-1-carboxylate (49.6 mg, 0.189 mmol) in DCM (1.25 ml_) was added to the new reaction and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After stirring at rt for 3 h, the resulting solution was added into the first reaction. After a further 16 h, saturated NaHC03(aq) (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography twice (0-100% EtOAc in cyclohexane; followed by 0%; then 25%; then 50% EtOAc in cyclohexane (isocratic)) to give the title compound (133 mg, 90%) as bright yellow foam. LCMS (Method A): RT = 1.62 min, m/z = 585, 587 [M+H]+.
133 mg		To a solution triphosgene (37.4 mg, 0.126 mmol) in DCM (2.5 mL) at 0 C was added pyridine (0.102 mL, 1.26 mmol). After 20 min, a solution of ferf-butyl ( )-3-phenylpiperazine-1-carboxylate (99.2 mg, 0.378 mmol) in DCM (2.5 mL) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After 3 h, the reaction mixture was transferred via syringe to flask containing (S)-4-chloro-1-((10-hydroxy-7-azaspiro[4.5]decan- 10-yl)methyl)pyridin-2(1 /-/)-one hydrochloride (84 mg, 0.252 mmol) before DIPEA (0.132 ml_, 0.756 mmol) was added. After stirring at rt for 4 days, the reaction had not reached full conversion so to a solution of triphosgene (18.7 mg, 0.063 mmol) in DCM (1.25 ml_) at 0 C in a separate flask was added pyridine (51 mI_, 0.630 mmol). After 20 min, a solution of tert- butyl ( )-3-phenylpiperazine-1-carboxylate (49.6 mg, 0.189 mmol) in DCM (1.25 ml_) was added to the new reaction and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After stirring at rt for 3 h, the resulting solution was added into the first reaction. After a further 16 h, saturated NaHC03(aq) (15 ml_) was added and the resulting mixture was extracted with DCM (3 x 10 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography twice (0-100% EtOAc in cyclohexane; followed by 0%; then 25%; then 50% EtOAc in cyclohexane (isocratic)) to give the title compound (133 mg, 90%) as bright yellow foam. LCMS (Method A): RT = 1.62 min, m/z = 585, 587 [M+H]+.

References: [1]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 298; 299.
[2]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 279-280.

19
[ 32315-10-9 ]
[ 1240584-34-2 ]
5-fluoro-1-((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-4-phenylpyridin-2(1H)-one [ No CAS ]
tert-butyl (3R)-4-(10-((5-fluoro-2-oxo-4-phenylpyridin-1-(2H)-yl)methyl)-10-hydroxy-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		To a solution (1873) triphosgene (6.2 mg, 0.0209 mmol) in THF (0.42 ml_) at 0 C was added pyridine (17 pl_, 0.210 mmol). After 30 min, a solution of te/f-butyl ( )-3-phenylpiperazine-1-carboxylate (16.6 mg, 0.0633 mmol) in THF (0.42 ml_) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After stirring for 4 h, 5-fluoro-1-((10- hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-4-phenylpyridin-2(1/-/)-one (8 mg, 0.0224 mmol) and DIPEA (37 mI_, 0.211 mmol) were added. The reaction was stirred at rt for 17 h before saturated sodium hydrogen carbonate (aq) solution (15 ml_) was added and the resulting mixture was extracted with DCM (3 x 10 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give the title compound (13.4 mg, 92%) as a light beige foam. LCMS (Method A): RT = 1.77 min, m/z = 645 [M+H]+.
92%		To a solution triphosgene (6.2 mg, 0.0209 mmol) in THF (0.42 mL) at 0 C was added pyridine (17 pL, 0.210 mmol). After 30 min, a solution of <strong>[1240584-34-2]tert-butyl (R)-3-phenylpiperazine-1-carboxylate</strong> (16.6 mg, 0.0633 mmol) in THF (0.42 mL) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After stirring for 4 h, 5-fluoro-1-((10- hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-4-phenylpyridin-2(1H)-one (8 mg, 0.0224 mmol) and DIPEA (37 pL, 0.211 mmol) were added. The reaction was stirred at rt for 17 h before saturated sodium hydrogen carbonate (aq) solution (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane; then 0-10% MeOH in EtOAc) to give the title compound (13.4 mg, 92%) as a light beige foam. LCMS (Method A): RT = 1.77 min, m/z = 645 [M+H]+.

References: [1]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 286.
[2]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 304; 305.

20
[ 32315-10-9 ]
[ 1240584-34-2 ]
3-fluoro-1-((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-4-phenylpyridin-2(1H)-one [ No CAS ]
tert-butyl (3R)-4-(10-((3-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)methyl)-10-hydroxy-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		To a solution of triphosgene (6.2 mg, 0.0210 mmol) in MeCN (0.42 ml_) at 0 C was added pyridine (17 pl_, 0.210 mmol). After 30 min, a solution of tert- butyl ( )-3-phenylpiperazine-1-carboxylate (16.6 mg, 0.0631 mmol) in MeCN (0.42 ml_) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After stirring for 4 h, 3-fluoro-1- ((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-4-phenylpyridin-2(1/-/)-one (15 mg, 0.0421 mmol) and DIPEA (37 mI_, 0.210 mmol) were added. The reaction was stirred at rt for 16 h before saturated NaHC03(aq) (15 ml_) was added and the resulting mixture was extracted with DCM (3 x 10 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane) to give title compound (22.9 mg, 84%) as an off-white foam. LCMS (Method A): RT = 1.77 min, m/z = 645 [M+H]+.
84%		To a solution of triphosgene (6.2 mg, 0.0210 mmol) in MeCN (0.42 ml_) at 0 C was added pyridine (17 pl_, 0.210 mmol). After 30 min, a solution of tenf-butyl (R)-3-phenylpiperazine-1-carboxylate (16.6 mg, 0.0631 mmol) in MeCN (0.42 ml.) was added and the reaction mixture was stirred at 0 C for a further 20 min before being allowed to warm to rt. After stirring for 4 h, 3-fluoro-1- ((10-hydroxy-7-azaspiro[4.5]decan-10-yl)methyl)-4-phenylpyridin-2(1 H)-one (15 mg, 0.0421 mmol) and DIPEA (37 pl_, 0.210 mmol) were added. The reaction was stirred at rt for 16 h before saturated NaHCO3(aq) (15 mL) was added and the resulting mixture was extracted with DCM (3 x 10 mL) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc in cyclohexane) to give title compound (22.9 mg, 84%) as an off-white foam. LCMS (Method A): RT = 1.77 min, m/z = 645 [M+H]+.

References: [1]Patent: WO2019/150119,2019,A1 .Location in patent: Page/Page column 288.
[2]Patent: WO2020/115501,2020,A1 .Location in patent: Page/Page column 306; 307.

21
[ 1240584-34-2 ]
1-((10-hydroxy-7-((R)-2-phenylpiperazine-1-carbonyl)-7-azaspiro[4.5]decan-10-yl)methyl) pyrazin-2(1H)-one [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

22
[ 1240584-34-2 ]
5-((10-hydroxy-7-((R)-2-phenylpiperazine-1-carbonyl)-7-azaspiro[4.5]decan-10-yl)methyl)-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

23
[ 1240584-34-2 ]
3-(((S)-4-hydroxy-3,3-dimethyl-1-((R)-2-phenylpiperazine-1-carbonyl)piperidin-4-yl)methyl)-6-phenylpyrimidin-4(3H)-one [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

24
[ 1240584-34-2 ]
4-chloro-1-(((S)-10-hydroxy-7-((R)-2-phenylpiperazine-1-carbonyl)-7-azaspiro[4.5]decan-10-yl)methyl)pyridin-2(1H)-one [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .
[2]Patent: WO2020/115501,2020,A1 .

25
[ 1240584-34-2 ]
4-cyclopropyl-1-(((S)-10-hydroxy-7-((R)-2-phenylpiperazine-1-carbonyl)-7-azaspiro[4.5]decan-10-yl)methyl)pyridin-2(1H)-one [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .
[2]Patent: WO2020/115501,2020,A1 .

26
[ 1240584-34-2 ]
1-(((S)-10-hydroxy-7-((R)-2-phenylpiperazine-1-carbonyl)-7-azaspiro[4.5]decan-10-yl)methyl)-4-(pyrrolidin-1-yl)pyridin-2(1H)-one [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .
[2]Patent: WO2020/115501,2020,A1 .

27
[ 1240584-34-2 ]
tert-butyl (3R)-4-(10-hydroxy-10-((2-oxopyrazin-1(2H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

28
[ 1240584-34-2 ]
tert-butyl (3R)-4-(10-hydroxy-10-((3-oxomorpholino)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

29
[ 1240584-34-2 ]
tert-butyl (3R)-4-(10-hydroxy-10-((6-oxo-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

30
[ 1240584-34-2 ]
tert-butyl (3R)-4-(10-hydroxy-10-((4-oxo-1-phenyl-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

31
[ 1240584-34-2 ]
tert-butyl (3R)-4-(10-hydroxy-10-((2-methyl-7-oxo-2,7-dihydro-6H-pyrazolo[4,3-d]pyrimidin-6-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

32
[ 1240584-34-2 ]
tert-butyl (3R)-4-(10-hydroxy-10-((1-methyl-4-oxo-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

33
[ 1240584-34-2 ]
tert-butyl (R)-4-((S)-10-hydroxy-10-((2-(methylthio)-5-oxopyrido[4,3-d]pyrimidin-6(5H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

34
[ 1240584-34-2 ]
tert-butyl (R)-4-((S)-10-hydroxy-10-((5-oxopyrido[4,3-d]pyrimidin-6(5H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

35
[ 1240584-34-2 ]
tert-butyl (R)-4-((S)-4-hydroxy-3,3-dimethyl-4-((6-oxo-4-phenylpyrimidin-1(6H)-yl)methyl)piperidine-1-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .

36
[ 1240584-34-2 ]
tert-butyl (R)-4-((S)-10-((4-cyclopropyl-2-oxopyridin-1(2H)-yl)methyl)-10-hydroxy-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .
[2]Patent: WO2020/115501,2020,A1 .

37
[ 1240584-34-2 ]
tert-butyl (R)-4-((S)-10-hydroxy-10-((2-oxo-4-(pyrrolidin-1-yl)pyridin-1(2H)-yl)methyl)-7-azaspiro[4.5]decane-7-carbonyl)-3-phenylpiperazine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2019/150119,2019,A1 .
[2]Patent: WO2020/115501,2020,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Lawesson's Reagent • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes

Related Functional Groups of
[ 1240584-34-2 ]

Aryls

A794107 [886766-73-0]

tert-Butyl 3-(m-tolyl)piperazine-1-carboxylate

Similarity: 1.00

A625626 [669695-60-7]

3-p-Tolyl-piperazine-1-carboxylic acid tert-butyl ester

Similarity: 1.00

A462072 [886766-85-4]

1-Boc-3-(4-Ethylphenyl)piperazine

Similarity: 1.00

A117495 [1240583-48-5]

(S)-tert-Butyl 2-phenylpiperazine-1-carboxylate

Similarity: 1.00

A236598 [859518-32-4]

(R)-tert-Butyl 2-phenylpiperazine-1-carboxylate

Similarity: 1.00

Amides

A794107 [886766-73-0]

tert-Butyl 3-(m-tolyl)piperazine-1-carboxylate

Similarity: 1.00

A625626 [669695-60-7]

3-p-Tolyl-piperazine-1-carboxylic acid tert-butyl ester

Similarity: 1.00

A462072 [886766-85-4]

1-Boc-3-(4-Ethylphenyl)piperazine

Similarity: 1.00

A117495 [1240583-48-5]

(S)-tert-Butyl 2-phenylpiperazine-1-carboxylate

Similarity: 1.00

A236598 [859518-32-4]

(R)-tert-Butyl 2-phenylpiperazine-1-carboxylate

Similarity: 1.00

Related Parent Nucleus of
[ 1240584-34-2 ]

Piperazines

A794107 [886766-73-0]

tert-Butyl 3-(m-tolyl)piperazine-1-carboxylate

Similarity: 1.00

A625626 [669695-60-7]

3-p-Tolyl-piperazine-1-carboxylic acid tert-butyl ester

Similarity: 1.00

A462072 [886766-85-4]

1-Boc-3-(4-Ethylphenyl)piperazine

Similarity: 1.00

A117495 [1240583-48-5]

(S)-tert-Butyl 2-phenylpiperazine-1-carboxylate

Similarity: 1.00

A236598 [859518-32-4]

(R)-tert-Butyl 2-phenylpiperazine-1-carboxylate

Similarity: 1.00

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Environmental hazards
Code	Phrase
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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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CAS No.: 1240584-34-2

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