144163-68-8|N-Methyl-1-(thiazol-2-yl)methanamine| Ambeed

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Quality Control of [ 144163-68-8 ] Purity: 98% SDS Specification

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Product Details of [ 144163-68-8 ]

CAS No. :	144163-68-8
Formula :	C₅H₈N₂S
M.W :	128.20
SMILES Code :	CNCC1=NC=CS1
MDL No. :	MFCD02854205
InChI Key :	MNHGOWYUJYMPGV-UHFFFAOYSA-N
Pubchem ID :	18939834

Safety of [ 144163-68-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 144163-68-8 ]

* 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.

Downstream synthetic route of [ 144163-68-8 ]

[ 144163-68-8 ] Synthesis Path-Downstream 1~38

1
[ 10200-59-6 ]
[ 593-51-1 ]
[ 144163-68-8 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

2
[ 30293-86-8 ]
[ 144163-68-8 ]
[ 144163-69-9 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

3
[ 144163-68-8 ]
[ 1026878-17-0 ]
(2R,3R)-2-(2,4-Difluoro-phenyl)-3-(N-methyl-N-thiazol-2-ylmethyl-aminosulfanyl)-1-[1,2,4]triazol-1-yl-butan-2-ol [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 85 - 94.

4
C₅H₆N₂S [ No CAS ]
[ 144163-68-8 ]

Yield	Reaction Conditions	Operation in experiment
		2- (N-Methylaminomethyl)Thiazole 70 [0227] To a flask containing dry DCM (60 mL) and 4A molecular sieves were added methylamine (2.0M solution in THF, 4.0 mL, 8.0 mmol), Na2S04 (1.42 g, 10.0 mmol), and 2-thiazolecarboxaldehyde (0.452 g, 4.0 mmol). The reaction mixture was stirred at room temperature and monitored by ¹H NMR. Upon completion, the reaction mixture filtered to remove the Na2S04 and molecular sieves and the filtrate was concentrated under reduced pressure. The crude imine was dissolved in absolute EtOH (40 mL), treated with NaBH4 (0.227 g, 6.0 mmol) and aged for several hours at rt (monitored by TLC). The reaction mixture was then quenched with water (8 mL) and concentrated under reduced pressure. The residue was treated with brine, extracted with DCM (3x50 mL), and the combined organic layers were dried, and evaporated under reduced pressure to give the desired product in 69% yield.

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.
[2]Patent: WO2005/123066,2005,A1 .Location in patent: Page/Page column 81.

5
[ 144163-68-8 ]
(2R,3R)-3-(2,4-Difluoro-phenyl)-3-hydroxy-4-[1,2,4]triazol-1-yl-butane-2-sulfonic acid methyl-thiazol-2-ylmethyl-amide [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 85 - 94.

6
[ 144163-68-8 ]
[ 1026867-26-4 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

7
[ 144163-68-8 ]
[ 144163-70-2 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

8
[ 144163-68-8 ]
(2S,3S,4S,5S)-5-amino-2-<N-<N-<<N-methyl-N-(2-thiazolylmethyl)amino>carbonyl>valinyl>amino>-3,4-dihydroxy-1,6-diphenylhexane [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

9
[ 144163-68-8 ]
(S)-N-{(1S,3S,4S)-1-Benzyl-2,3-dihydroxy-4-[(S)-3-methyl-2-(3-methyl-3-pyridin-2-ylmethyl-ureido)-butyrylamino]-5-phenyl-pentyl}-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyramide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

10
[ 144163-68-8 ]
(S)-2-[3-(2-Amino-thiazol-4-ylmethyl)-3-methyl-ureido]-N-{(1S,3S,4S)-1-benzyl-2,3-dihydroxy-4-[(S)-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyrylamino]-5-phenyl-pentyl}-3-methyl-butyramide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

11
[ 144163-68-8 ]
[ 144164-00-1 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

12
[ 144163-68-8 ]
(S)-N-{(1S,3R,4S)-1-Benzyl-2,3-dihydroxy-4-[(S)-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyrylamino]-5-phenyl-pentyl}-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyramide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

13
[ 144163-68-8 ]
(S)-N-{(1S,2S,3S,4S)-1-Benzyl-2,3-dihydroxy-4-[(S)-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyrylamino]-5-phenyl-pentyl}-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyramide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

14
[ 144163-68-8 ]
(S)-N-{(1S,2R,3R,4S)-1-Benzyl-2,3-dihydroxy-4-[(S)-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyrylamino]-5-phenyl-pentyl}-3-methyl-2-(3-methyl-3-thiazol-2-ylmethyl-ureido)-butyramide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330.

16
[ 1285701-39-4 ]
[ 144163-68-8 ]
[ 1222874-96-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 60℃; for 2.0h;	General Procedure: Chloride 8 (0.10 g, 0.35 mmol) was dissolved in DMF (2 mL). Diisopropylethylamine (0.12 mL, 0.70 mmol) and (2-methylthiazol-4-yl)methanamine (0.07 mg, 0.53 mmol) were added and the reaction was stirred at 60 C for 18 h. The crude solution was purified directly by HPLC (Waters 2525 HPLC, Gradient of 20% -> 60% acetonitrile in water) and lyophilized to yield amine 45 as a pure solid.

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3152 - 3158.

17
[ 144163-68-8 ]
[ 1569653-73-1 ]

References: [1]Patent: WO2014/31873,2014,A2 .

18
[ 144163-68-8 ]
[ 1569656-51-4 ]

References: [1]Patent: WO2014/31873,2014,A2 .

19
[ 769-56-2 ]
[ 144163-68-8 ]
[ 1569653-80-0 ]

Yield	Reaction Conditions	Operation in experiment
14%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃;Inert atmosphere; Sealed tube;	4,6-dibromobenzo[c][l ,2,5]oxadiazole (1.1509 g, 4.14 mmol) and N-methyl-l-(thiazol-2- yl)methanamine (4.97 mmol) were massed into a tube. The tube was evacuated and flushed with argon for three cycles. NMP (6 mL) and DIPEA (0.94 mL, 5.38 mmol) were then added and the tube was sealed and heated to 100 C overnight. Upon cooling to room temperature the mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was back- extracted with EtOAc. The combined organic layers were then washed with water (5x), brine, dried (Na2S04), filtered and concentrated to give an oil. The crude oil was then purified via flash column chromatography (30 % EtOAc / hexane) to afford 0.1872 g (14 % yield) of aniline. This aniline (0.1872 g, 0.58 mmol) and 3-formylphenylboronic acid (0.0899 g, 0.60 mmol) were massed into a tube. The tube was evacuated and purged with argon (3x). DME (1.5 mL) and 2M Na2C03 (0.9 mL, 1.74 mmol) were then added followed by Pd(PPh3)4 (0.0335 g, 0.029 mmol). The tube was then sealed and heated to 85 C overnight. Upon cooling to room temperature the mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was back-extracted with EtOAc. The combined organic layers were then washed with water (5x), brine, dried (Na2S04), filtered and concentrated to give an oil. This crude oil was then dissolved in THF (4 mL) and cooled to 0 C. CF3TMS (0.17 mL, 1.16 mmol) was added followed by TBAF (0.06 mL, 1.0 M solution in THF). The reaction was then stirred for 60 minutes before re- cooling to 0C and 4N HC1 (aq) was added and stirred for 60 minutes. The mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was basified. The aqueous layer was then re-extracted with EtOAc. The combined organic layers were was with water, brine, dried (Na2S04), filtered and concentrated to give a crude oil. This material was purified via flash column chromatography with step-gradient (100 % DCM to 0.5 % MeOH / DCM) to afford 0.0339 g (14 % yield, 3 steps) of TRV-1459. *H NMR (CDC13, 700 MHz) δ = 7.77 (d, J = 3.2 Hz, 1H), 7.73 (s, 1H), 7.66 (dt, J = 7.2, 1.6 Hz, 1H), 7.55-7.51 (m, 2H), 7.31 (s, 1H), 7.30 (d, J = 3.2 Hz, 1H), 6.46 (s, 1H), 5.46 (s, 2H), 5.13 (q, J = 6.6 Hz, 1H), 3.32 (s, 3H).

References: [1]Patent: WO2014/31873,2014,A2 .Location in patent: Paragraph 0159.

20
C₁₆H₁₅ClN₂O₅S [ No CAS ]
[ 144163-68-8 ]
C₂₁H₂₂N₄O₅S₂ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.

21
[ 144163-68-8 ]
C₁₅H₁₉N₃OS [ No CAS ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.

22
[ 144163-68-8 ]
C₂₈H₃₅N₅O₆S₂ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.

23
[ 144163-68-8 ]
C₂₂H₃₂N₄O₂S [ No CAS ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.
[3]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.
[4]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.

24
[ 144163-68-8 ]
C₃₂H₄₉N₅O₅S [ No CAS ]

25
[ 144163-68-8 ]
C₂₇H₄₁N₅O₃S*C₂HF₃O₂ [ No CAS ]

26
[ 144163-68-8 ]
C₃₃H₅₂N₆O₄S [ No CAS ]

27
[ 144163-68-8 ]
C₄₇H₆₉N₇O₇S [ No CAS ]

28
[ 144163-68-8 ]
C₄₂H₆₁N₇O₅S*C₂HF₃O₂ [ No CAS ]

29
[ 144163-68-8 ]
micromide [ No CAS ]

30
[ 144163-68-8 ]
C₃₉H₅₅N₇O₈S₂ [ No CAS ]

31
[ 144163-68-8 ]
C₂₇H₄₀N₄O₄S [ No CAS ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.

32
[ 37553-65-4 ]
[ 144163-68-8 ]
C₂₀H₂₇N₃O₃S [ No CAS ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7232 - 7238.

33
C₁₉H₁₅N₇O₃ [ No CAS ]
[ 144163-68-8 ]
TM-N₁₅₇₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 886 - 898.

34
(4S,6S,E)-8-(2-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-1,3-dithian-2-yl)-2,4,6-trimethyloct-2-enoic acid [ No CAS ]
[ 144163-68-8 ]
tert-butyl methyl(3-(2-((3S,5S,E)-3,5,7-trimethyl-8-(methyl-(thiazol-2-ylmethyl)amino)-8-oxooct-6-en-1-yl)-1,3-dithian-2-yl)-propyl)carbamate [ No CAS ]

References: [1]Journal of Organic Chemistry,2017,vol. 82,p. 1705 - 1718.

35
(4R,6S,E)-8-(2-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-1,3-dithian-2-yl)-2,4,6-trimethyloct-2-enoic acid [ No CAS ]
[ 144163-68-8 ]
tert-butyl methyl(3-(2-((3S,5R,E)-3,5,7-trimethyl-8-(methyl-(thiazol-2-ylmethyl)amino)-8-oxooct-6-en-1-yl)-1,3-dithian-2-yl)-propyl)carbamate [ No CAS ]

References: [1]Journal of Organic Chemistry,2017,vol. 82,p. 1705 - 1718.

36
(4R,6R,E)-8-(2-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-1,3-dithian-2-yl)-2,4,6-trimethyloct-2-enoic acid [ No CAS ]
[ 144163-68-8 ]
tert-butyl methyl(3-(2-((3R,5R,E)-3,5,7-trimethyl-8-(methyl-(thiazol-2-ylmethyl)amino)-8-oxooct-6-en-1-yl)-1,3-dithian-2-yl)-propyl)carbamate [ No CAS ]

References: [1]Journal of Organic Chemistry,2017,vol. 82,p. 1705 - 1718.

37
(4S,6R,E)-8-(2-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-1,3-dithian-2-yl)-2,4,6-trimethyloct-2-enoic acid [ No CAS ]
[ 144163-68-8 ]
tert-butyl methyl(3-(2-((3R,5S,E)-3,5,7-trimethyl-8-(methyl-(thiazol-2-ylmethyl)amino)-8-oxooct-6-en-1-yl)-1,3-dithian-2-yl)-propyl)carbamate [ No CAS ]

References: [1]Journal of Organic Chemistry,2017,vol. 82,p. 1705 - 1718.

38
5-[3-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]oxy}-2-iodopyrimidine [ No CAS ]
[ 144163-68-8 ]
5-[3-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]oxy}-N-methyl-N-(thiazol-2-ylmethyl)pyrimidine-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl acetamide; at 120℃; for 1.0h;	Compound (I-191) (30.0 mg, 0.071 mmol) was dissolved in 1,4-dioxane (0.6 mL)/DMA (0.6 mL) mixed solution,<strong>[144163-68-8]N-methyl-1-(thiazol-2-yl)methanamine</strong> (20.0 mg, 0.156 mmol) and DIPEA (50 mL, 0.29 mmol) were added and the mixturewas stirred at 120C for 2 hr. The reaction mixture was allowed to cool, water was added and the mixture was extractedwith ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporatedunder reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate) to givecompound (I-194) (yield 3.3 mg, 11%) as a colorless oil
11%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl acetamide; at 120℃; for 2.0h;	Compound (1-191) (30.0 mg, 0.071 mmol)Was dissolved in 1,4-dioxane (0.6 mL) / DMA (0.6 mL)After dissolving in the mixed solution,N-methyl-1- (thiazol-2-yl) methanamine (20.0 mg, 0.156 mmol) and DIPEA(50 μL, 0.29 mmol)And the mixture was stirred at 120 C. for 2 hours.After leaving the reaction solution to cool,Water was added and the mixture was extracted with ethyl acetate.The organic layer was dried over anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography(n-hexane: ethyl acetate)Compound (1-194)(Yield 3.3 mg, Yield 11%)As a colorless oil.

References: [1]Patent: EP3351533,2018,A1 .Location in patent: Paragraph 0467.
[2]Patent: JP2018/145180,2018,A .Location in patent: Paragraph 0437.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 144163-68-8 ]

Amines

A159379 [680591-00-8]

Ethyl-thiazol-2-ylmethyl-amine

Similarity: 0.98

A345249 [93714-84-2]

N-(Thiazol-2-ylmethyl)formamide

Similarity: 0.95

A288400 [55661-33-1]

Thiazol-2-ylmethanamine

Similarity: 0.92

A490356 [792185-36-5]

N-(Thiazol-2-ylmethyl)propan-2-amine

Similarity: 0.91

A206373 [850852-85-6]

Thiazol-2-ylmethanamine hydrochloride

Similarity: 0.90

Related Parent Nucleus of
[ 144163-68-8 ]

Thiazoles

A159379 [680591-00-8]

Ethyl-thiazol-2-ylmethyl-amine

Similarity: 0.98

A345249 [93714-84-2]

N-(Thiazol-2-ylmethyl)formamide

Similarity: 0.95

A288400 [55661-33-1]

Thiazol-2-ylmethanamine

Similarity: 0.92

A490356 [792185-36-5]

N-(Thiazol-2-ylmethyl)propan-2-amine

Similarity: 0.91

A206373 [850852-85-6]

Thiazol-2-ylmethanamine hydrochloride

Similarity: 0.90

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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

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

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CAS No.: 144163-68-8

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