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Quality Control of [ 124045-51-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 124045-51-8 ]

CAS No. :	124045-51-8	MDL No. :	MFCD22548360
Formula :	C₉H₁₅NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QVMLIHFGUIRVKU-UHFFFAOYSA-N
M.W :	169.22	Pubchem ID :	18366137
Synonyms :

Safety of [ 124045-51-8 ]

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Hazard Statements:	H315-H319-H335-H227	Packing Group:
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Application In Synthesis of [ 124045-51-8 ]

* 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 [ 124045-51-8 ]

[ 124045-51-8 ] Synthesis Path-Downstream 1~8

1
[ 100367-77-9 ]
[ 124045-51-8 ]
[ 1312712-19-8 ]

Yield	Reaction Conditions	Operation in experiment
55%		To a solution of <strong>[100367-77-9]ethyl 2-bromothiazole-4-carboxylate</strong> (4, 5.0 g, 21 mmol) in 15ml of dry degassed THF was added diisopropylamine (3.2 g, 32 mmol),followed by CuI (0.2 g, 1.0 mmol) and Pd(PPh3)2Cl2 (0.7 g, 1.0 mmol). Afterstirring 5 min at RT, methyl-prop-2-ynyl-carbamic acid tert-butyl ester (3.5 g,21 mmol) was added dropwise to the reaction mixture over 5 min. After stirringovernight at RT, reaction mixture was diluted with tetrahydrofurane and filteredthrough celite. Solvent was then evaporated and the resulting crude mixture waspurified by column chromatography on silica gel using ethyl acetate /cyclohexane 3:7 as eluent to give ethyl 2-[3-[tertbutoxycarbonyl(methyl)amino]prop-1-ynyl]thiazole-4-carboxylate (5, 3.8 g, 12mmol, 55 %).
47%		Example 1 : This example illustrates the preparation of 2-(3-{methyl-[2-(5-methyl-3- trifluoromethyl-pyrazol-1 -yl)-acetyl]-amino}-propyl)-thiazole-4-carboxylic acid methyl-(R)- 1 ,2,3,4-tetrahydro-naphthalen-1-yl-amide (Compound No. 1.d.55) a) Preparation of 2-[3-(tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]-thiazole-4-carboxylic acid ethyl ester1 To a solution of <strong>[100367-77-9]ethyl 2-bromothiazole-4-carboxylate</strong> (3.54 g, 15 mmol) in dry degassed THF (10 mL) was added diisopropylamine (2.27 g, 22.5 mmol), followed by Cul (0.14 g, 0.75 mmol) and Pd(PPh3)2CI2 (0.52 g, 0.75 mmol). After stirring 5 min at RT, methyl-prop-2-ynyl-carbamic acid tert-butyl ester2 (2.54 g, 15 mmol) was added dropwise to the reaction mixture over 5 min. After stirring overnight at RT, reaction mixture was diluted with THF (20 mL) and filtered through celite. Solvent was then evaporated and the resulting crude mixture was purified by column chromatography on silica gel(ethylacetate/cyclohexane 3:7) to give 2-[3-(tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]- thiazole-4-carboxylic acid ethyl ester (2.32 g, 47 %). 1H-NMR (400 MHz, CDCI3): delta = 8.15 (s, 1 H), 4.49-4.42 (q, 2H), 4.38-4.26 (m, 2H), 2.95 (s, 3H), 1.49 (s, 9H), 1.43-1.393 (t, 3H) . MS: m/z = 347 (M+23).
47%	With diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20℃;Inert atmosphere;	a) Preparation of 2-[3-(tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]-thiazole-4-carboxylic acid ethyl ester1 1 For similar Sonogashira reaction, see Wipf, P., Wang, Z. WO 2008/106080.To a solution of <strong>[100367-77-9]ethyl 2-bromothiazole-4-carboxylate</strong> (3.54 g, 15 mmol) in dry degassed THF (10 mL) was added diisopropylamine (2.27 g, 22.5 mmol), followed by CuI (0.14 g, 0.75 mmol) and Pd(PPh3)2Cl2 (0.52 g, 0.75 mmol). After stirring 5 min at RT, methyl-prop-2-ynyl-carbamic acid tert-butyl ester2 (2.54 g, 15 mmol) was added dropwise to the reaction mixture over 5 min. After stirring overnight at RT, reaction mixture was diluted with THF (20 mL) and filtered through celite. Solvent was then evaporated and the resulting crude mixture was purified by column chromatography on silica gel (ethylacetate/cyclohexane 3:7) to give 2-[3-(tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]-thiazole-4-carboxylic acid ethyl ester (2.32 g, 47%). 1H-NMR (400 MHz, CDCl3): delta=8.15 (s, 1H), 4.49-4.42 (q, 2H), 4.38-4.26 (m, 2H), 2.95 (s, 3H), 1.49 (s, 9H), 1.43-1.393 (t, 3H). MS: m/z=347 (M+23). 2 For the synthesis of methyl-prop-2-ynyl-carbamic acid tert-butyl ester, see Bradbury, B. J.; Baumgold, J.; Jacobson, K. A J. Med. Chem. 1990, 33, 741-8.

Reference： [1]Synlett,2017,vol. 28,p. 2277 - 2280
[2]Patent: WO2011/76510,2011,A1 .Location in patent: Page/Page column 34
[3]Patent: US2012/258990,2012,A1 .Location in patent: Page/Page column 15

2
[ 105170-27-2 ]
[ 124045-51-8 ]
C₁₅H₂₀N₂O₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2373 - 2379

3
[ 16066-84-5 ]
[ 106-96-7 ]
[ 124045-51-8 ]

Yield	Reaction Conditions	Operation in experiment
33%		To a solution of tert-butyl N-methylcarbamate (10.4 g, 79.2 mmol) in THF (120 mL) was added NaH (4.12 g, 103 mmol, 60% purity) under 0 C. The mixture was stirred at 0 C. for 0.5 hour, then 3-bromoprop-1-yne (13.2 g, 111 mmol) was added dropwise. The mixture was stirred at rt for 16 hours. On completion, the reaction mixture was quenched with water (10 mL) at 0 C., and then concentrated in vacuo to give a residue. The residue was diluted with water (80 mL) and extracted with DCM (4×60 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography to give the title compound (4.50 g, 33% yield) as light yellow oil. 1H NMR (400 MHz, DMSO-d6) delta 4.05 (s, 2H), 2.92 (s, 3H), 2.22 (t, J=2.4 Hz, 1H), 1.47 (s, 9H).
0.56g		(Step 2) A solution of 17 (0.77 g, 5.9 mmol) in DMF (13 mL) was treated with sodium hydride(60 wt.% in oil, 0.29 g, 7.3 mmol) at 0 C under an argon atmosphere. After stirring for 15 min at roomtemperature, 3-bromo-1-propyne (0.65 mL, 8.6 mmol) was added to the mixture at 0 C. The mixture was stirred for 2.5 h at room temperature and quenched with saturated aqueous ammonium chloride at 0 C.Extractive workup and purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 10/1as the eluent) afforded tert-butyl methyl(prop-2-yn-1-yl)carbamate (18) (0.56 g, 56% yield) as a yellow oil.

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 3002; 3003
[2]Tetrahedron,2015,vol. 71,p. 554 - 559

4
[ 877624-40-3 ]
[ 124045-51-8 ]
methyl 6-(3-((tert-butoxycarbonyl)(methyl)amino)prop-1-yn-1-yl)-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In 1,4-dioxane; at 50℃;	A solution of Example 1.21.5 (1.97 g), tert-butyl methyl(prop-2-yn-1-yl)carbamate (1 g), bis(triphenylphosphine)palladium(II) dichloride (0.19 g), CuI (0.041 g), and triethylamine (2.25 mL) in 20 mL dioxane was stirred at 50 C. overnight. The mixture was then concentrated and chromatographed on silica gel using 10-50% ethyl acetate in heptanes to give the title compound.

Reference： [1]Patent: US2016/158377,2016,A1 .Location in patent: Paragraph 0763

5
[ 39856-57-0 ]
[ 124045-51-8 ]
tert-butyl ((5-bromo-1H-pyrrolo[3.2-b]pyridin-2-yl)methyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
515 mg	With pyrrolidine; bis-triphenylphosphine-palladium(II) chloride; at 20 - 60℃; for 23h;Inert atmosphere;	A mixture of <strong>[39856-57-0]2,6-dibromopyridin-3-amine</strong> (0.50g, 1.985 mmol, Manchester Organics), tert- butyl methyl(prop-2-yn-1-yl)carbamate Intermediate 11 (0.403 g, 2.382 mmol), pyrrolidine (1.641 ml, 19.85 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.070 g, 0.099 mmol) was stirred at room temperature under nitrogen for 5 hours and then at 60C for 18 hours. The solvent was removed in vacuo. The residue was dissolved in DCM and applied to a 120g silica cartridge. This was eluted with a gradient of 0-100% ethyl acetate in cyclohexane over 30 minutes. The required fractions were combined and evaporated in vacuo to give tert-butyl ((5-bromo-1H-pyrrolo[3,2-b]pyridin-2- yl)methyl)(methyl)carbamate (515 mg) as a brown oil. LCMS (System B, UV, ESI): Rt = 1.0 5 min, [M+H]+ 340 + 342

Reference： [1]Patent: WO2019/115640,2019,A1 .Location in patent: Page/Page column 50; 90

6
[ 1050501-88-6 ]
[ 124045-51-8 ]
tert-butyl _ (3-(3-amino-6-chloropyridin-2-yl)prop-2-yn-1-yl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 70℃; for 17h;Inert atmosphere; Sealed tube;	A mixture of tert-butyl methyl(prop-2-yl-1-yl)carbamate (612 mg, 3.62 mmol, Intermediate 11), <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (500 mg, 2.410 mmol, Fluorochem), copper I iodide (51 mg, 0.268 mmol, Sigma), PdCI2(dppf) (148 mg, 0.202 mmol, Manchester Organics) and TEA (0.504 ml_, 3.62 mmol, Sigma) in a sealed vial was degassed (purged and filled with nitrogen x 3) before adding anhydrous Tetrahydrofuran (THF) (10 ml_). The suspension was degassed by bubbling nitrogen through for 2 min. The reaction mixture was heated to 70 C for 17 hr. The reaction mixture was filtered through a 2.5g Celite SPE, eluting with ethyl actetate (30 ml.) and water (10 ml_). The reaction mixture was diluted with water (20 ml_), the aqueous extracted with ethyl acetate (3 x 30 ml_), combined organics washed with brine (20 ml_), dried through a hydrophobic frit and concentrated in vacuo and under nitrogen to give tert-butyl (3-(3-amino-6-chloropyridin-2-yl)prop-2-yn-1- yl)(methyl)carbamate (1.074 g, 2.360 mmol, 98 % yield) as a brown oil. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 1.45 - 1.56 (m, 12 H) 3.00 (s, 3 H) 4.34 (s, 2 H) 6.96 - 7.13 (m, 2 H). LCMS (System B, UV, ESI) Rt = 1.08 min, [M+H]+ 240, 242

Reference： [1]Patent: WO2019/115640,2019,A1 .Location in patent: Page/Page column 47; 62

7
[ 1050501-88-6 ]
[ 124045-51-8 ]
tert-butyl ((5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.339 g	With pyrrolidine; bis-triphenylphosphine-palladium(II) chloride; In water; ethyl acetate; at 60℃; for 7h;	A mixture of <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (11.15g, 53.7 mmol, Fluorochem), Intermediate 44 tert-butyl methyl(prop-2-yn-1-yl)carbamate (13.64 g, 81 mmol), pyrrolidine (22.22 ml, 269 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.886 g, 2.69 mmol) was stirred and heated at 60C for 7 hours, LCMS showed mainly cyclised product. The reaction mixture was separated between ethyl acetate (250ml) and water (100ml). The organic phase was washed with brine (100ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The residue was dissolved in DCM and applied to a 330g silica cartridge. This was eluted with a gradient of 0- 100% ethyl acetate in cyclohexane over 30 minutes. The required fractions were combined and evaporated in vacuo to give tert-butyl ((5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methyl)(methyl)- carbamatetert-butyl methyl(prop-2-yn-1-yl)carbamate (9.339g) as a tan solid. LCMS (System B, UV, ESI): Rt = 1.03 min, [M+H]+ 296

Reference： [1]Patent: WO2019/115640,2019,A1 .Location in patent: Page/Page column 49; 79-80

8
[ 26166-92-7 ]
[ 124045-51-8 ]
tert-butyl N-[3-[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-5-yl]prop-2-ynyl]-N-methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 80℃; for 0.5h;	1 Step 1-Tert-butyl N-[3-[2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindolin-5-yl]prop-2-ynyl]-N-methyl-carbamate To a mixture of tert-butyl N-methyl-N-prop-2-ynyl-carbamate (1.00 g, 5.93 mmol, Intermediate IY) and 5-bromo-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione (1.00 g, 2.97 mmol, Intermediate GA) in DMF (4 mL) was added CuI (56.4 mg, 296 umol), TEA (5.40 g, 53.3 mmol, 7.43 mL) and Pd(PPh3)2Cl2 (208 mg, 296 umol). The reaction mixture was heated at 80° C. for 0.5 hour under microwave. On completion, the reaction mixture was diluted with water (30 mL) and extracted with EA (3×50 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography to give the title compound (1.20 g, 95% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 11.14 (s, 1H), 7.96-7.88 (m, 3H), 5.16 (dd, J=5.6, 12.8 Hz, 1H), 4.33 (s, 2H), 3.33 (s, 3H), 2.89-2.83 (m, 1H), 2.64-2.51 (m, 2H), 2.10-2.02 (m, 1H), 1.42 (s, 9H).

Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - US2019/192668, 2019, A1 Location in patent: Paragraph 3031; 3032

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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. 124045-51-8 ] {[proInfo.proName]}

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[ 124045-51-8 ] Synthesis Path-Downstream 1~8

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