[ CAS No. 1400589-53-8 ] {[proInfo.proName]}

Name: 1400589-53-8|(R)-tert-Butyl 2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate|97%
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Quality Control of [ 1400589-53-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1400589-53-8 ]

CAS No. :	1400589-53-8	MDL No. :	MFCD30478724
Formula :	C₁₇H₂₂ClN₅O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OFZCHVIWFAEDMH-LLVKDONJSA-N
M.W :	379.84	Pubchem ID :	86706988
Synonyms :

Safety of [ 1400589-53-8 ]

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

Application In Synthesis of [ 1400589-53-8 ]

* 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 [ 1400589-53-8 ]
Downstream synthetic route of [ 1400589-53-8 ]

[ 1400589-53-8 ] Synthesis Path-Upstream 1~5

1
[ 1174913-80-4 ]
[ 1379338-74-5 ]
[ 1400589-53-8 ]

Yield	Reaction Conditions	Operation in experiment
7.7 g	With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 130℃; for 0.666667 h; Microwave irradiation	Intermediate 22: 1,1-Dimethylethyl (2R)-2-[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-4-morpholinecarboxylate 1,1-dimethylethyl (2R)-2-(aminomethyl)-4-morpholinecarboxylate (for preparation see: J. Medicinal Chemistry, 2009, 52 (15), 4810-4819) (6 g, 27.7 mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60 mL) and to this was added DIPEA (7.27 mL, 41.6 mmol) and 5,7-dichloropyrido[3,4-b]pyrazine (5.55 g, 27.7 mmol). This was split between 4 large microwave vials and each was heated at 130° C. for 30 min. They were monitored by LCMS and were given a further 10 min at 130° C. The reaction mixtures were partitioned between ethyl acetate (700 ml) and diluted aqueous ammonium chloride (1 litre). The aqueous was reextracted with ethyl acetate (300 ml) and the combined organics were washed with aqueous ammonium chloride (500 ml), dried over sodium sulfate and concentrated in vacuo to yield a crude brown oil. It was dissolved in DCM and passed through silica (70 g) eluting with DCM (640 ml) then 5percent ethyl acetate in DCM (240 ml), 10percent ethyl acetate in DCM (540 ml) then 15percent ethyl acetate in DCM (240 ml) then 20percent ethyl acetate in DCM (2*40 ml). Appropriate fractions were combined and concentrated in vacuo to yield: N8231-100-2, orange-yellow slightly gummy solid, 7.7 g LCMS (Method B): Rt=1.17 min, MH⁺380

Reference： [1] Patent: WO2012/123312, 2012, A1, . Location in patent: Page/Page column 73-74
[2] Patent: US2014/5188, 2014, A1, . Location in patent: Paragraph 0621; 0622; 0623

2
[ 101079-63-4 ]
[ 1400589-53-8 ]

Reference： [1] Patent: WO2012/123312, 2012, A1,
[2] Patent: US2014/5188, 2014, A1,

3
[ 2587-02-2 ]
[ 1400589-53-8 ]

Reference： [1] Patent: WO2012/123312, 2012, A1,
[2] Patent: US2014/5188, 2014, A1,

4
[ 2897-43-0 ]
[ 1400589-53-8 ]

Reference： [1] Patent: WO2012/123312, 2012, A1,
[2] Patent: US2014/5188, 2014, A1,

5
[ 2587-03-3 ]
[ 1400589-53-8 ]

Reference： [1] Patent: WO2012/123312, 2012, A1,
[2] Patent: US2014/5188, 2014, A1,

[ 1400589-53-8 ] Synthesis Path-Downstream 1~14

1
[ 101079-63-4 ]
[ 1400589-53-8 ]

Reference： [1]Patent: WO2012/123312,2012,A1
[2]Patent: US2014/5188,2014,A1

2
[ 2587-02-2 ]
[ 1400589-53-8 ]

Reference： [1]Patent: WO2012/123312,2012,A1
[2]Patent: US2014/5188,2014,A1

3
[ 2897-43-0 ]
[ 1400589-53-8 ]

Reference： [1]Patent: WO2012/123312,2012,A1
[2]Patent: US2014/5188,2014,A1

4
[ 1400589-53-8 ]
[ 761446-44-0 ]
[ 1400589-54-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 8.0h;Reflux; Inert atmosphere;Product distribution / selectivity;	Intermediate 23: 1 ,1 -Dimethylethyl (2f~)-2-(fr7-(1-methyl-1H-pyrazol-4- yl)pyridor3,4-/3lpyrazin-5-yl1amino)methyl)-4-morpholinecarboxylate; A mixture of 1 , 1-dimethylethyl (2f~)-2-[(7-chloropyrido[3,4-b]pyrazin-5- yl)amino]methyl}-4-morpholinecarboxylate (0.4g, 1.053mmol), 1-methyl-4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (0.263g, 1.264mmol) and cesium carbonate (0.858g, 2.63mmol) in 1 ,4-dioxane (15ml_) and Water (4ml_) was degassed with nitrogen. Tetrakis(triphenylphosphine)palladium (0) (0.049g, 0.042mmol) was added and this was heated under reflux for 8h. The reaction had gone to completion, and the crude mixture was cooled.A scale-up was carried out in which a mixture of 1 , 1-dimethylethyl (2R)-2-[(7- chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-4-morpholinecarboxylate (6.3g, 16.59mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (3.80g, 18.24mmol) and caesium carbonate (11.89g, 36.5mmol) in 1 ,4-dioxane (150ml_) and Water (35 ml_) was degassed with nitrogen and to this was added tetrakis(triphenylphosphine)palladium (0) (0.383g, 0.332mmol). This was degassed with nitrogen and heated under reflux for 16h. The reaction had gone to completion and so was cooled.These two reaction mixtures were combined and worked up as follows:The combined crude material was partitioned between ethyl acetate and aqueous ammonium chloride. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo to yield a crude product. It was dissolved in DCM and purified through silica (70g) eluting with X% ethyl acetate in DCM where X=0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90 (1X40ml of each), followed by 25 X 40ml of ethyl acetate. Appropriate fractions were combined and concentrated in vacuo to yield the title compound, greyish-gold foam/solid, 7.8g.LCMS (Method C): rt =0.83min, MH+ =426
7.8 g	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; for 16.0h;Inert atmosphere; Reflux;	Intermediate 23: 1,1-Dimethylethyl (2R)-2-([7-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-b]pyrazin-5-yl]amino}methyl)-4-morpholinecarboxylate A mixture of <strong>[1400589-53-8]1,1-dimethylethyl (2R)-2-[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-4-morpholinecarboxylate</strong> (0.4 g, 1.053 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.263 g, 1.264 mmol) and cesium carbonate (0.858 g, 2.63 mmol) in 1,4-dioxane (15 mL) and Water (4 mL) was degassed with nitrogen. Tetrakis(triphenylphosphine)palladium (0) (0.049 g, 0.042 mmol) was added and this was heated under reflux for 8 h. The reaction had gone to completion, and the crude mixture was cooled. A scale-up was carried out in which a mixture of <strong>[1400589-53-8]1,1-dimethylethyl (2R)-2-[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-4-morpholinecarboxylate</strong> (6.3 g, 16.59 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3.80 g, 18.24 mmol) and caesium carbonate (11.89 g, 36.5 mmol) in 1,4-dioxane (150 mL) and Water (35 mL) was degassed with nitrogen and to this was added tetrakis(triphenylphosphine)palladium (0) (0.383 g, 0.332 mmol). This was degassed with nitrogen and heated under reflux for 16 h. The reaction had gone to completion and so was cooled. These two reaction mixtures were combined and worked up as follows: The combined crude material was partitioned between ethyl acetate and aqueous ammonium chloride. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo to yield a crude product. It was dissolved in DCM and purified through silica (70 g) eluting with X % ethyl acetate in DCM where X=0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90 (1×40 ml of each), followed by 25×40 ml of ethyl acetate. Appropriate fractions were combined and concentrated in vacuo to yield the title compound, greyish-gold foam/solid, 7.8 g. LCMS (Method C): rt=0.83 min, MH+=426

Reference： [1]Patent: WO2012/123312,2012,A1 .Location in patent: Page/Page column 74-75
[2]Patent: US2014/5188,2014,A1 .Location in patent: Paragraph 0624-0629

5
[ 2587-03-3 ]
[ 1400589-53-8 ]

Reference： [1]Patent: WO2012/123312,2012,A1
[2]Patent: US2014/5188,2014,A1

6
[ 1174913-80-4 ]
[ 1379338-74-5 ]
[ 1400589-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 130℃; for 0.666667h;microwave irradiation;	Intermediate 22: 1 ,1-Dimethylethyl (2/~)-2-{r(7-chloropyridor3,4-6lpyrazin-5- yl)amino1methylV4-morpholinecarboxylate; 1 , 1-dimethylethyl (2f~)-2-(aminomethyl)-4-morpholinecarboxylate (for preparation see: J. Medicinal Chemistry, 2009, 52 (15), 4810-4819) (6g, 27.7mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60ml_) and to this was added DIPEA (7.27ml_, 41.6mmol) and <strong>[1379338-74-5]5,7-dichloropyrido[3,4-b]pyrazine</strong> (5.55g, 27.7mmol). This was split between 4 large microwave vials and each was heated at 130C for 30min. They were monitored by LCMS and were given a further 10min at 130C. The reaction mixtures were partitioned between ethyl acetate (700ml) and diluted aqueous ammonium chloride (1 litre). The aqueous was reextracted with ethyl acetate (300ml) and the combined organics were washed with aqueous ammonium chloride (500ml), dried over sodium sulfate and concentrated in vacuo to yield a crude brown oil. It was dissolved in DCM and passed through silica (70g) eluting with DCM (6 X 40ml) then 5% ethyl acetate in DCM (2 X 40ml), 10% ethyl acetate in DCM (5 X 40ml) then 15% ethyl acetate in DCM (2 X 40ml) then 20%ethyl acetate in DCM (2 X 40ml). Appropriate fractions were combined and concentrated in vacuo to yield: N8231-100-2, orange-yellow slightly gummy solid, 7.7gLCMS (Method B): Rt = 1.17min, MH+ 380
7.7 g	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 130℃; for 0.666667h;Microwave irradiation;	Intermediate 22: 1,1-Dimethylethyl (2R)-2-[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-4-morpholinecarboxylate 1,1-dimethylethyl (2R)-2-(aminomethyl)-4-morpholinecarboxylate (for preparation see: J. Medicinal Chemistry, 2009, 52 (15), 4810-4819) (6 g, 27.7 mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60 mL) and to this was added DIPEA (7.27 mL, 41.6 mmol) and <strong>[1379338-74-5]5,7-dichloropyrido[3,4-b]pyrazine</strong> (5.55 g, 27.7 mmol). This was split between 4 large microwave vials and each was heated at 130 C. for 30 min. They were monitored by LCMS and were given a further 10 min at 130 C. The reaction mixtures were partitioned between ethyl acetate (700 ml) and diluted aqueous ammonium chloride (1 litre). The aqueous was reextracted with ethyl acetate (300 ml) and the combined organics were washed with aqueous ammonium chloride (500 ml), dried over sodium sulfate and concentrated in vacuo to yield a crude brown oil. It was dissolved in DCM and passed through silica (70 g) eluting with DCM (640 ml) then 5% ethyl acetate in DCM (240 ml), 10% ethyl acetate in DCM (540 ml) then 15% ethyl acetate in DCM (240 ml) then 20% ethyl acetate in DCM (2*40 ml). Appropriate fractions were combined and concentrated in vacuo to yield: N8231-100-2, orange-yellow slightly gummy solid, 7.7 g LCMS (Method B): Rt=1.17 min, MH+ 380

Reference： [1]Patent: WO2012/123312,2012,A1 .Location in patent: Page/Page column 73-74
[2]Patent: US2014/5188,2014,A1 .Location in patent: Paragraph 0621; 0622; 0623

7
[ 1400589-53-8 ]
7-(1-methyl-1H-pyrazol-4-yl)-N-[(2S)-2-morpholinylmethyl]pyrido[3,4-b]pyrazin-5-amine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2012/123312,2012,A1

8
[ 1400589-53-8 ]
[ 1400589-94-7 ]

Reference： [1]Patent: WO2012/123312,2012,A1
[2]Patent: US2014/5188,2014,A1

9
[ 1400589-53-8 ]
[ 1415794-52-3 ]

Reference： [1]Patent: WO2012/167733,2012,A1

10
[ 1400589-53-8 ]
[ 1415792-65-2 ]

Reference： [1]Patent: WO2012/167733,2012,A1

11
[ 1400589-53-8 ]
[ 1415794-62-5 ]
[ 1415794-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110.0℃;Inert atmosphere;	(A) (S)-terf -butyl 2-((7-(4-(piperazi n-1 -yl)phenyl)pyrido[4,3-£>]pyrazi n-5- ylami no)methyl)morpholi ne-4-carboxylateA solution of (S)-ferf-butyl 2-((7-chloropyrido[4,3-£>]pyrazin-5- ylamino)nnethyl)nnorpholine-4-carboxylate (3.96 g, 10.43 mmol), 1 -(4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)piperazine hydrochloride (4.4 g, 13.55 mmol), Pd(PPh3) (2.41 g, 2.09 mmol) and Cs2CO3 (10.19 g, 31 .29 mmol) in 150 mL of dioxane and 3 mL of water, under N2, was stirred at 1 10 C overnight. The volatiles were removed in vacuo, and the residues was purified by chromatography with MeOH/H2O ( 1 :20~5:1 ) to give 4.747 g of title compound. MS (m/z) = 506 (M+H)+.

Reference： [1]Patent: WO2012/167733,2012,A1 .Location in patent: Page/Page column 156

12
[ 1400589-53-8 ]
[ 1400586-28-8 ]

Reference： [1]Patent: US2014/5188,2014,A1

13
[ 1400589-53-8 ]
[ 1415794-30-7 ]

Reference： [1]Patent: US2014/121200,2014,A1

14
[ 1400589-53-8 ]
[ 1415794-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethyl acetate; at 20.0℃; for 2.0h;	The <strong>[1400589-53-8](R)-tert-butyl 2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate</strong> (3.00 g, 8.0 mmol) was dissolved in the solution of HCl in ethyl acetate (20 mL), and the mixture was stirred at room temperature for 2 hours until TLC indicated Boc group was removed. The volatile materials were removed in vacuo and the residues were dissolved in dichloromethane.

Reference： [1]Patent: US2014/121200,2014,A1 .Location in patent: Paragraph 0362; 0363

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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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. 1400589-53-8 ] {[proInfo.proName]}

Quality Control of [ 1400589-53-8 ]

Related Doc. of [ 1400589-53-8 ]

Product Details of [ 1400589-53-8 ]

Safety of [ 1400589-53-8 ]

Application In Synthesis of [ 1400589-53-8 ]

[ 1400589-53-8 ] Synthesis Path-Upstream 1~5

[ 1400589-53-8 ] Synthesis Path-Downstream 1~14

Related Functional Groups of [ 1400589-53-8 ]

Chlorides

Amides

Amines

Related Parent Nucleus of [ 1400589-53-8 ]

Other Aromatic Heterocycles

Morpholines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1400589-53-8 ]

Related Parent Nucleus of
[ 1400589-53-8 ]