[ CAS No. 1038866-44-2 ]

Name: Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride
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SKU: A175310
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Quality Control of [ 1038866-44-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1038866-44-2 ]

CAS No. :	1038866-44-2	MDL No. :	MFCD21608029
Formula :	C₁₁H₁₄ClN₃O₂	Boiling Point :	834.9°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	255.70	Pubchem ID :	66687106
Synonyms :

Computed Properties of [ 1038866-44-2 ]

TPSA :Topological Polar Surface Area	63.2	H-Bond Acceptor Count :	4
XLogP3 :	-	H-Bond Donor Count :	3
SP3 :	0.45	Rotatable Bond Count :	0

Safety of [ 1038866-44-2 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1038866-44-2 ]

Upstream synthesis route of [ 1038866-44-2 ]
Downstream synthetic route of [ 1038866-44-2 ]

[ 1038866-44-2 ] Synthesis Path-Upstream 1~2

1
[ 883984-95-0 ]
[ 1038866-44-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrogen In ethanol at 20℃; for 9.00 h;	Step 3: spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride 16.4 g (42.4 mmol) benzyl 7'-chloro-2'-oxo-1'.2'-dihydrospiro[piperidine-4,4'-pyrido[2,3d][1,3]oxazine]-1-carboxylate and 2.00 g palladium(Pd/C 10percent) in 500 mL EtOH were hydrogenated in a hydrogen atmosphere for 6 h at RT. Then another 1.0 g palladium (Pd/C 10percent) were added the mixture was hydrogenated for a further 3 h at RT in a hydrogen atmosphere. After filtration of the reaction mixture the solvent was eliminated in vacuo. The residue was triturated with EtOH, the precipitate formed was suction filtered, washed with EtOH and dried. Yield: 5.40 g (50percent of theoretical) ESI-MS: m/z=220 (M+H)⁺ R_t(HPLC): 0.90 min (method C)
50%	With hydrogen In ethanol at 20℃; for 9.00 h;	Step 3: spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride 16.40 g (0.04 mol) benzyl 7'-chloro-2'-oxo-1',2'-dihydrospiro[piperidine-4,4'-pyrido[2,3d]-[1,3]oxazine]-1-carboxylate and 2.00 g palladium(Pd/C 10percent) in 500 mL EtOH were hydrogenated for 6 h at RT in a hydrogen atmosphere. Then 1 g of palladium (Pd/C 10percent) were additionally added and the mixture was hydrogenated for a further 3 h at RT in a hydrogen atmosphere. After filtration of the reaction mixture the solvent was eliminated in vacuo. The residue was triturated with EtOH, the precipitate formed was suction filtered, washed with EtOH and dried in the drying cupboard for 3 h at 50° C.Yield: 5.40 g (50percent of theoretical)ESI-MS: m/z=220 (M+H)⁺ R_t(HPLC): 0.90 min (method C)

Reference： [1] Patent: US2011/21500, 2011, A1. Location in patent: Page/Page column 46
[2] Patent: US2012/149698, 2012, A1. Location in patent: Page/Page column 26

2
[ 45644-21-1 ]
[ 1038866-44-2 ]

Reference： [1] Patent: US2012/149698, 2012, A1

[ 1038866-44-2 ] Synthesis Path-Downstream 1~10

1
[ 1038866-44-2 ]
[ 1185274-82-1 ]
[ 7693-46-1 ]
[ 1185274-53-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of (7lambda)-4-chloro-10-[l-(trifluoromethyl)cyclopropyl]-3,6,7,12- tetrahydroimidazo[r,2':l,7]azepino[3,4-e]indazol-7-amine (100 mg, 0.3 mmol)],and triethylamine (120 uL, 0.9 mmole) is added p-nitrophenyl chloroformate (60 mg, 0.3 mmmol) and stirred at 0C for 1 hr. Spiro[piperidine-4,4'-pyrido[2,3-d][l,3]oxazin]-2'(1'H)-one hydrochloride [Burgey et ah WO 2006/044504], (77 mg, 0.3mmole is then added with triethylamine (120 uL, 0.675 mmol) and the reaction mixture is stirred at ambient temperature for 16 hrs. Saturated aqueous sodium carbonate (50 mL) is added and the mixture is extracted with dichloromethane (3 * 25 mL). The organic layer is washed with saturated aqueous sodium bicarbonate (3 x), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane ? 93% dichloromethane/ methanol] gives the title compound

Reference： [1]Patent: WO2009/105348,2009,A1.Location in patent: Page/Page column 40

2
[ 45644-21-1 ]
[ 1038866-44-2 ]

Reference： [1]Patent: US2012/149698,2012,A1

3
[ 1038866-44-2 ]
[ 1231750-45-0 ]
[ 1231749-28-2 ]

Yield	Reaction Conditions	Operation in experiment
25%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 10h;	Example 781-{1-[6-(2.7-dimethyl-3H-benzimidazol-5-yloxy)-pyrimidin-4-yl]-spiro[piperidin-4,4'-pyrido-[2,3-d][1,3]oxazin]-2'(1'H)-one; 128 mg (0.500 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 167 mg (0.500 mmol) 6-(6-chloro-pyrimidin-4-yloxy)-2-methyl-4-trifluoromethyl-1H-benzimidazole and 0.261 mL (1.50 mmol) DIPEA in 1.5 mL DMF were stirred for 10 h at RT. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were combined and freeze-dried.Yield: 65 mg (25% of theory)ESI-MS: m/z=512 (M+H)+ Rt (HPLC): 3.0 min (method C)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 102

4
[ 1038866-44-2 ]
[ 1231750-39-2 ]
[ 1231749-17-9 ]

Yield	Reaction Conditions	Operation in experiment
17%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃;	Example 671-(6-(2-methoxy-7-methyl-1H-benzo[d]imidazol-5-yloxy)pyrimidin-4-yl)spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one; 64 mg (0.25 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 57 mg (0.20 mmol) 5-(6-chloropyrimidin-4-yloxy)-2-methoxy-7-methyl)-1H-benzo[d]-imidazole and 130 muL (0.75 mmol) DIPEA in 2.0 mL DMF were stirred overnight at 60 C. The reaction mixture was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with a 1M aqueous NaOH solution. The precipitate formed was suction filtered, washed and dried.Yield: 20 mg (17% of theory)ESI-MS: m/z=474 (M+H)+ Rt(HPLC): 1.10 min (method B)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 99

5
[ 1038866-44-2 ]
[ 1231750-29-0 ]
[ 1231749-12-4 ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50℃;	Example 631-(6-(7-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazol-5-yloxy)pyrimidin-4-yl)spiro-[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one; 21 mg (0.08 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 22 mg (0.07 mmol) 5-(6-chloropyrimidin-4-yloxy)-7-methyl-2-(trifluoromethyl)-1H-benzo[d]-imidazole and 40 muL (0.24 mmol) DIPEA in 2.0 mL DMF were stirred at 50 C. over the weekend. The reaction mixture was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with a 1M aqueous NaOH solution. The precipitate formed was suction filtered, washed and dried.Yield: 18 mg (44% of theory)ESI-MS: m/z=512 (M+H)+ Rt(HPLC): 1.30 min (method B)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 98

6
[ 1038866-44-2 ]
[ 1231750-18-7 ]
[ 1231749-06-6 ]

Yield	Reaction Conditions	Operation in experiment
18%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃;	Example 581-(6-(7-methyl-2-(tetrahydrofuran-3-yl)-1H-benzo[d]imidazol-5-yloxy)pyrimidin-4-yl)spiro-[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one; 138 mg (0.54 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 180 mg (0.54 mmol) 5-(6-chloropyrimidin-4-yloxy)-7-methyl-2-(tetrahydrofuran-3-yl)-1H-benzo[d]imidazole and 280 muL (1.62 mmol) DIPEA in 5.0 mL DMF were stirred overnight at 60 C. The reaction mixture was combined with ice water. The precipitate formed was suction filtered and purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with an aqueous NaHCO3 solution and extracted with ethyl acetate. The organic phase was dried and evaporated down i.vac.Yield: 50 mg (18% of theory)ESI-MS: m/z=514 (M+H)+ Rt(HPLC): 2.88 min (method L)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 97

7
[ 1038866-44-2 ]
[ 1231749-69-1 ]
[ 1231749-21-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 60℃;	Example 714-methyl-6-(2-methyl-6-(2'-oxo-1'.2'-dihydrospiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-1-yl)pyrimidin-4-yloxy)benzo[d]oxazol-2(3H)-one; 90 mg (0.35 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 90 mg (0.31 mmol) 6-(6-chloro-2-methylpyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one and 200 muL (1.16 mmol) DIPEA in 1.5 mL DMF were stirred overnight at RT. Another 90 mg (0.35 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong> and 200 muL (1.16 mmol) DIPEA were added and the mixture was stirred for 8 h at 60 C. The reaction mixture was mixed with water and stirred overnight. Then DCM was added and the mixture was stirred for a further 30 min. DCM was removed and the aqueous phase was suction filtered. The precipitate was washed with EtOH and dried.Yield: 100 mg (68% of theory)ESI-MS: m/z=475 (M+H)+ Rt(HPLC): 1.04 min (method B)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 100

8
[ 1038866-44-2 ]
[ 1231750-41-6 ]
[ 1231749-26-0 ]

Yield	Reaction Conditions	Operation in experiment
36%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 1h;	Example 754-(4-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-6-yloxy)-6-(2'-oxo-1'.2'-dihydrospiro-[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-1-yl)nicotinonitrile; 40 mg (0.16 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 40 mg (0.12 mmol) 6-chloro-4-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-yloxy)-nicotino-nitrile and 0.08 mL (0.47 mmol) DIPEA in 0.80 mL NMP were stirred for 1 h at 140 C. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were partially evaporated down i.vac. and neutralised with aqueous NaHCO3 solution. The precipitate formed was suction filtered and dried.Yield: 47 mg (36% of theory)ESI-MS: m/z=485 (M+H)+ Rt(HPLC): 1.34 min (method B)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 101-102

9
[ 1038866-44-2 ]
[ 1231750-49-4 ]
[ 1231749-20-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50℃;	Example 70(R)-1-(6-(4-methyl-2-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-6-yloxy)pyrimidin-4-yl)-spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one; 166 mg (0.65 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 205 mg (0.62 mmol) (R)-6-(6-chloropyrimidin-4-yloxy)-4-methyl-2-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazole and 320 muL (1.86 mmol) DIPEA in 5.0 mL DMF were stirred overnight at 50 C. The reaction mixture was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with an aqueous NaHCO3 solution. The precipitate formed was suction filtered, washed and dried.Yield: 110 mg (35% of theory)ESI-MS: m/z=514 (M+H)+ Rt(HPLC): 0.98 min (method B)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 100

10
[ 1038866-44-2 ]
[ 1231750-48-3 ]
[ 1231749-18-0 ]

Yield	Reaction Conditions	Operation in experiment
38%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	Example 681-(6-(7-methyl-1H-indazol-5-yloxy)pyrimidin-4-yl)spiro[piperidin-4,4'-pyrido[2,3-d]-[1,3]oxazin]-2'(1'H)-one; 60 mg (0.23 mmol) <strong>[1038866-44-2]spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride</strong>, 60 mg (0.23 mmol) 5-(6-chloropyrimidin-4-yloxy)-7-methyl-1H-indazole and 100 muL (0.58 mmol) DIPEA in 0.8 mL DMF were stirred at RT over the weekend. The reaction mixture was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with an aqueous saturated NaHCO3 solution. The precipitate formed was suction filtered and dried.Yield: 40 mg (38% of theory)ESI-MS: m/z=444 (M+H)+ Rt(HPLC): 3.06 min (method C)

Reference： [1]Patent: US2012/88755,2012,A1.Location in patent: Page/Page column 99-100

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Ghs Precautionary Statements

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P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
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

[ CAS No. 1038866-44-2 ]

Quality Control of [ 1038866-44-2 ]

Related Doc. of [ 1038866-44-2 ]

Product Details of [ 1038866-44-2 ]

Computed Properties of [ 1038866-44-2 ]

Safety of [ 1038866-44-2 ]

Application In Synthesis of [ 1038866-44-2 ]

[ 1038866-44-2 ] Synthesis Path-Upstream 1~2

[ 1038866-44-2 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 1038866-44-2 ]

Amides

Related Parent Nucleus of [ 1038866-44-2 ]

Other Aromatic Heterocycles

Piperidines

Spiroes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 1038866-44-2 ]

Related Parent Nucleus of
[ 1038866-44-2 ]