5952-93-2|Methyl 1-methyl-1H-pyrazole-4-carboxylate| Ambeed

CAS No. :	5952-93-2
Formula :	C₆H₈N₂O₂
M.W :	140.14
SMILES Code :	O=C(C1=CN(C)N=C1)OC
MDL No. :	MFCD11053755
InChI Key :	HGQQQXMARFJNCP-UHFFFAOYSA-N
Pubchem ID :	10130004

Safety of [ 5952-93-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 5952-93-2 ]

* 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 [ 5952-93-2 ]

[ 5952-93-2 ] Synthesis Path-Downstream 1~31

1
[ 110860-60-1 ]
[ 88398-85-0 ]
[ 5952-93-2 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1545 - 1547.

2
[ 67-56-1 ]
[ 5952-92-1 ]
[ 5952-93-2 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 778 - 784.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 1071 - 1077.

3
[ 5952-93-2 ]
[ 39806-90-1 ]
[ 34091-53-7 ]
[ 34091-52-6 ]
methyl ester of 3,5-diiodo-1-methylpyrazole-4-carboxylic acid [ No CAS ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 778 - 784.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 1071 - 1077.

4
[ 5952-93-2 ]
[ 88398-85-0 ]
[ 109056-69-1 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 537 - 540.

5
methyl 3-amino-1-methylpyrazole-4-carboxylate [ No CAS ]
[ 5952-93-2 ]
[ 148934-66-1 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 537 - 540.

6
[ 624-49-7 ]
[ 256658-45-4 ]
[ 78607-37-1 ]
[ 22050-80-2 ]
[ 5952-93-2 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 8849 - 8853.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 4 Methyl-1-methyl-4-pyrazole-carboxylate A stirred mixture of 1.12 g DI-water, 5.92 g concentrated aqueous HCl and 2.08 g NH2 -NHCH3 was cooled to 15 C. and 10.00 g 3,3-dimethoxy-2-dimethoxymethyl-propionate were fed within 5 minutes. The mixture was stirred at 15 C. to 20 C. for 2.0 hours and, afterwards, approximately two-thirds of the solvent was removed in vacuo. The precipitated crystalline product was removed by suction-filtration, washed with a small amount of ice water and subsequently dried in vacuo. By this means, 4.00 g (63% of theory based on 3,3-dimethoxy-2-dimethoxymethyl-propionate) methyl-1-methyl4-pyrazole-carboxylate could be isolated. Identification of the product was based on 1 H-NMR-, 13 C- and IR-spectra. The mother liquor still contained methyl-1-methyl-4-pyrazole-carboxylate.
	With caesium carbonate; In acetonitrile; at 20℃;Cooling with ice;	General procedure: To a mixture of 1H-pyrrole-3-carboxylic acid (1.0 g, 9.00 mmol) and cesium carbonate (1.58 mL, 19.80 mmol) in ACN (20 mL) colled in an ice bath, was added iodomethane (1.68 mL, 27.0 mmol). The resulting mixture was stirred at RT. The mixture was then filtered, and the solid was washed with EtOAc. The filtrate was concentrated and dried under reduced pressure to give methyl 1-methyl-1H-pyrrole-3-carboxylate (577 mg). LCMS- ESI (pos.): 140.1 (M+H)+.

8
[ 5952-93-2 ]
[ 109056-69-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sulfuryl dichloride; In dichloromethane; at 20℃; for 12h;	Sulphuryl chloride (14.4 mL,178.35 mmol) was added to a solution of compound 1 (5 g, 35.68 mmol) in dichloromethane (100 mL) and the resulting mixture was stirred at room temperature for 12 h. The reaction mixture was poured into saturated aqueous solution of sodium bicarbonate (40 mL) and extracted with dichloromethane (2 × 20 mL). The combined extracts were washed with brine solution (3 × 25 mL), dried over sodium sulphate (22 g), filtered and evaporated in vacuo to obtain the crude product. The crude compound was crystallized using cyclohexane (30 mL) to afford compound 1. White powder; Yield: 7 g, 94 %; m.p.: 58-59 C. 1H NMR (300 MHz, CDCl3): delta 3.85 (s, 3H, -OMe),3.82 (s, 3H, -NMe); ESI-MS: m/z, 209 (M+1)+.

References: [1]Asian Journal of Chemistry,2017,vol. 29,p. 1477 - 1481.
[2]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 537 - 540.

9
[ 5952-93-2 ]
[ 109056-72-6 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 537 - 540.
[2]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 537 - 540.
[3]Asian Journal of Chemistry,2017,vol. 29,p. 1477 - 1481.

10
[ 5952-93-2 ]
[ 100784-27-8 ]

11
[ 5952-93-2 ]
halosulfuron methyl [ No CAS ]

12
[ 5952-92-1 ]
[ 18107-18-1 ]
[ 5952-93-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With methanol; In hexanes; at 0℃; for 0.333333h;	[00263] Step A: (Trimethylsilyl)diazomethane (12.0 niL, 24 mmol, 2.0M solution in hexanes) was added dropwise via an addition funnel to a cold (O0C) solution of 1 -methyl- IH- pyrazole-4-carboxylic acid (0.59 g, 4.7 mmol) in MeOH (20 mL). The reaction mixture was stirred for 20 minutes and then concentrated. The crude product was partitioned between ethyl acetate (100 mL) and water (50 mL). The organics were dried, filtered and concentrated. The crude product was purified by flash chromatography, eluting with hexanes/ethyl acetate (4:1) to give methyl 1 -methyl- lH-pyrazole-4-carboxylate (0.50 g, 3.6 mmol, 76% yield) as a solid, m/z (APCI-pos) M+l = 141.1.

References: [1]Patent: WO2011/25951,2011,A1 .Location in patent: Page/Page column 54.

13
[ 39806-90-1 ]
[ 67-56-1 ]
[ 201230-82-2 ]
[ 5952-93-2 ]

References: [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6903 - 6908.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 6418 - 6430.

14
[ 5952-93-2 ]
[ 170020-91-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine; In methanol; at 20℃; for 24h;	General procedure: To a solution of methyl 1-(methylcarbamoyl)-1H-pyrazole-3- carboxylate, Example 395.1 (0.943 g, 5.15 mmol) in MeOH (10 mL, 247 mmol), was added hydrazine (0.236 mL, 10.30 mmol) at RT. The resulting mixture was stirred at RT for 24 h. The mixture was then concentrated in vacuo and the residue was dissolved in water (100 mL). The aqueous solution was lyophilized to give the title compound (943 mg). LCMS-ESI (pos.): 184.1 (M+H)+.

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2613 - 2616.
[2]Patent: WO2018/97945,2018,A1 .Location in patent: Paragraph 0668; 0674.

15
[ 5952-93-2 ]
[ 1174309-68-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2613 - 2616.

16
[ 5952-93-2 ]
[ 1216061-43-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2613 - 2616.

17
[ 5952-93-2 ]
[ 1412407-44-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2613 - 2616.

18
[ 5952-93-2 ]
C₁₈H₁₈N₆OS [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2613 - 2616.

19
[ 5952-93-2 ]
[ 1610361-24-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2613 - 2616.

20
[ 39971-65-8 ]
[ 5952-93-2 ]
methyl 1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 11868 - 11871.
Angew. Chem.,2014,vol. 126,p. 12062 - 12065,4.

21
1-[bis(difluoroacetoxy)iodo]-3,5-di-tert-butylbenzene [ No CAS ]
[ 5952-93-2 ]
methyl-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 5126 - 5129.

22
[ 5952-93-2 ]
methyl 3-chloro-5-(chlorosulfonyl)-1-methyl-1H-pyrazole-4-carboxylate [ No CAS ]

References: [1]Asian Journal of Chemistry,2017,vol. 29,p. 1477 - 1481.

23
[ 5952-93-2 ]
(S)-benzyl-3-(((4-(methoxycarbonyl)-1-methyl-1H-pyrazol-5-yl)methyl)amino)-piperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2018/2437,2018,A1 .

24
[ 5952-93-2 ]
(S)-5-(((1-((benzyloxy)carbonyl)piperidin-3-yl)amino)methyl)-1-methyl-1H-pyrazole-4-carboxylic acid [ No CAS ]

References: [1]Patent: WO2018/2437,2018,A1 .

25
[ 5952-93-2 ]
(S)-benzyl-3-(1-methyl-4-oxopyrrolo[3,4-c]pyrazol-5(1H,4H,6H)-yl)piperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2018/2437,2018,A1 .

26
[ 5952-93-2 ]
(S)-1-methyl-5-(piperidin-3-yl)-5,6-dihydropyrrolo[3,4-c]pyrazol-4(1H)-one [ No CAS ]

References: [1]Patent: WO2018/2437,2018,A1 .

27
[ 5952-93-2 ]
5-((S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-yl)-1-methyl-5,6-dihydropyrrolo[3,4-c]pyrazol-4(1H)-one [ No CAS ]

References: [1]Patent: WO2018/2437,2018,A1 .

28
[ 68-12-2 ]
[ 5952-93-2 ]
methyl-5-formyl-1-methyl-1H-pyrazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.2 g		To a stirred solution of LDA (2.0 M in THF) (10.7 mL, 21.42 mmol) in THF (10.0 mL) was added methyl 1-methyl- 1H-pyrazole-4-carboxylate (1.0 g, 7.14 mmol) in THF (10.0 mL) at -78 C slowly and stirred for 2 h. Dimethylformamide (2.5 mL, 32.84 mmol) was added to the reaction mixture at -78C and then allowed to stir at 0 C for 2 h. The reaction mixture was quenched with aqueous 1 M HC1 solution (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Crude product was purified with silica gel chromatography using20% EtOAc / petroleum ether to afford 0.200 g of methyl 5-formyl-i-methyl-1H-pyrazole-4- carboxylate as pale yellow solid.?H NMR (400 MHz, CDC13) oe ppm 3.91 (s, 3H), 4.20 (s, 3H), 7.91 (s, 1H), 10.50 (s, 1H).

References: [1]Patent: WO2018/2437,2018,A1 .Location in patent: Page/Page column 96; 97.

29
[ 5952-93-2 ]
[ 756-79-6 ]
dimethyl (2-(1-methyl-1H-pyrazol-4-yl)-2-oxoethyl)phosphonate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733.

30
[ 5952-93-2 ]
2-(5H-imidazo[5,1-a]isoindol-5-yl)-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733.

31
[ 5952-93-2 ]
2-(5H-imidazo[5,1-a]isoindol-5-yl)-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-ol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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Code	Phrase
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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.
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Physical hazards
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H200	Unstable explosive
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H250	Catches fire spontaneously if exposed to air
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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
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
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H312	Harmful in contact with skin
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H372	Causes damage to organs through prolonged or repeated exposure
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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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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Product Details of [ 5952-93-2 ]

Safety of [ 5952-93-2 ]

Application In Synthesis of [ 5952-93-2 ]

[ 5952-93-2 ] Synthesis Path-Downstream 1~31

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