[ CAS No. 3034-41-1 ]

Name: 3034-41-1|1-Methyl-4-nitroimidazole|95%
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Quality Control of [ 3034-41-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3034-41-1 ]

Product Details of [ 3034-41-1 ]

CAS No. :	3034-41-1	MDL No. :	MFCD00159683
Formula :	C₄H₅N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HSCOLDQJZRZQMV-UHFFFAOYSA-N
M.W :	127.10	Pubchem ID :	18209
Synonyms :

Calculated chemistry of [ 3034-41-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.31
TPSA :	63.64 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.81
Log Po/w (XLOGP3) :	-0.44
Log Po/w (WLOGP) :	0.33
Log Po/w (MLOGP) :	0.06
Log Po/w (SILICOS-IT) :	-1.67
Consensus Log Po/w :	-0.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.7
Solubility :	25.6 mg/ml ; 0.201 mol/l
Class :	Very soluble
Log S (Ali) :	-0.43
Solubility :	47.1 mg/ml ; 0.371 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.14
Solubility :	92.5 mg/ml ; 0.728 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.08

Safety of [ 3034-41-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3034-41-1 ]

* 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 [ 3034-41-1 ]
Downstream synthetic route of [ 3034-41-1 ]

[ 3034-41-1 ] Synthesis Path-Upstream 1~9

1
[ 553-90-2 ]
[ 3034-38-6 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960

2
[ 616-47-7 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, 1924, vol. 125, p. 1434
[2] Synthesis, 2011, # 17, p. 2859 - 2864

3
[ 3034-38-6 ]
[ 77-78-1 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Liebigs Annalen der Chemie, 1987, p. 77 - 80
[2] Journal of the Chemical Society, 1925, vol. 127, p. 576
[3] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960

4
[ 616-47-7 ]
[ 3034-41-1 ]
[ 3034-42-2 ]
[ 19183-15-4 ]

Reference： [1] Synthesis, 2011, # 17, p. 2859 - 2864

5
[ 212248-40-3 ]
[ 74-88-4 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 12, p. 1764 - 1766

6
[ 186581-53-3 ]
[ 60-29-7 ]
[ 3034-38-6 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, 1925, vol. 127, p. 576

7
[ 3034-38-6 ]
[ 77-78-1 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, 1925, vol. 127, p. 576

8
[ 616-47-7 ]
[ 3034-41-1 ]
[ 5213-50-3 ]
[ 19183-20-1 ]
[ 1671-82-5 ]

Yield	Reaction Conditions	Operation in experiment
1%	at 110 - 120℃; for 2 h;	Nitration of 1-methylimidazole with Nitric Acid and Sulfuric Acid Fuming nitric acid (1.5 ml, excess, d.1.544 g/ml) was added to 1-methylimidazole (100 mg, 1.22 mmol) at room temperature with stirring. Then sulfuric acid (1.5 ml, excess, fuming 30percent SO₃) was added slowly from the top of condenser. After addition, the reaction mixture was heated to 110° C. and then the reaction temperature was maintained between 110-120° C. for 2.0 hrs. The reaction mixture was cooled to room temperature and the resulting mixture of products was extracted with methylene chloride and the organic phase was dried with Na₂SO₄/NaHCO₃. Evaporation of the solvent gave 61 mg of oil. Proton NMR showed that the ratio of the products was 7:25:45:2:1 (corresponding to 1-methyl-4-nitroimidazole, 1-methyl-2-nitroimidazole, 1-methyl-4,5-dinitroimidazole, 1-methyl-2,4-dinitroimidazole, and 1-methyl-2,4,5-trinitroimidazole). The yield of 1-methyl-2,4,5-trinitroimidazole is less then 1percent based on the integration of the NMR.

Reference： [1] Patent: US7304164, 2007, B1, . Location in patent: Page/Page column 7

9
[ 3034-41-1 ]
[ 89088-69-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 1, p. 144 - 158
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 265 - 285

[ 3034-41-1 ] Synthesis Path-Downstream 1~61

1
[ 616-47-7 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1]Journal of the Chemical Society,1924,vol. 125,p. 1434
[2]Synthesis,2011,p. 2859 - 2864

2
[ 3034-41-1 ]
[ 74-88-4 ]
[ 3034-43-3 ]

Reference： [1]Journal of the Chemical Society,1924,vol. 125,p. 1434
[2]Journal of the Chemical Society,1924,vol. 125,p. 1434
[3]Chemical Communications,2005,p. 2750 - 2752

3
[ 186581-53-3 ]
[ 60-29-7 ]
[ 3034-38-6 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 576

4
[ 3034-38-6 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 77-78-1 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 576

5
[ 3034-38-6 ]
[ 77-78-1 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1]Liebigs Annalen der Chemie,1987,p. 77 - 80
[2]Journal of the Chemical Society,1925,vol. 127,p. 576
[3]Tetrahedron Letters,1984,vol. 25,p. 1957 - 1960

6
[ 3034-43-3 ]
[ 3034-41-1 ]

Reference： [1]Journal of the Chemical Society,1924,vol. 125,p. 1434
[2]Journal of the Chemical Society,1924,vol. 125,p. 1434

7
[ 54828-05-6 ]
[ 3034-41-1 ]

Reference： [1]Helvetica Chimica Acta,1924,vol. 7,p. 714

8
[ 527-69-5 ]
[ 3034-41-1 ]
[ 62366-35-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1977,p. 145 - 158

9
[ 3034-41-1 ]
[ 7205-98-3 ]
[ 116271-00-2 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1987,vol. 35,p. 287 - 292
[2]Chemistry - A European Journal,2008,vol. 14,p. 6108 - 6118

10
[ 3034-41-1 ]
[ 79578-98-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃;	Example 268b 1-Methyl-1H-imidazol-4-amine 268b A 100-mL round-bottomed flask was charged with 268a (1.6 g, 12.6 mmol), 10% palladium on carbon (50% wet, 160 mg), and ethanol (15 mL). The flask was evacuated, charged with hydrogen gas, and stirred at room temperature overnight. The catalyst was removed by filtration through a pad of CELITE and the filtrate was concentrated under reduced pressure to afford 268b (1.2 g, 98%) as a yellow solid. MS-ESI: [M+H]+ 98.2
92%	With hydrogen;palladium 10% on activated carbon; In ethanol; for 1.5h;	Step B: To l-methyl-4-nitro-lH-imidazole (354 mg, 2.8 mmol) inEtOH (20 mL) was added 10%> Pd-C (90 mg) and the mixture was stirred under a hydrogen atmosphere for 1.5 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford 1 -methyl- lH-imidazol-4-amine (250 mg, 92%) as a yellow oil that darkened upon standing. 1H NMR (300 MHz, DMSO- d6) delta 7.05 (s, 1H), 6.08 (d, J= 1.3 Hz, 1H), 4.06 (br s, 2H), 3.47 (s, 3H).
92%	With palladium 10% on activated carbon; hydrogen; In ethanol;	Step B: To <strong>[3034-41-1]1-methyl-4-nitro-1H-imidazole</strong> (354 mg, 2.8 mmol) in EtOH (20 mL) was added 10% Pd-C (90 mg) and the mixture was stirred under a hydrogen atmosphere for 1.5 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford 1-methyl-1H-imidazol-4-amine (250 mg, 92%) as a yellow oil that darkened upon standing. 1H NMR (300 MHz, DMSO-d6) delta 7.05 (s, 1H), 6.08 (d, J=1.3 Hz, 1H), 4.06 (br s, 2H), 3.47 (s, 3H).

89%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h;	[0280j To a solution of i-methyl-4-nitro-1H-imidazole (500 mg, 3.94 mmol) in MeOH (10 mL) was added Pd/C (50 mg). The mixture was stirred at rt for 16 h under hydrogen atmosphere. Then the mixture was filtered and the filtrate was concentrated in vacuo. The crude product (340 mg. yield: 89%) was used in the next step without further purification. ESI-MS (M+H): 98.1.
82%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 25℃; for 12h;	Under hydrogen (1 atm), to a solution of compound <strong>[3034-41-1]1-methyl-4-nitro-1H-imidazole</strong> (500 mg, 3.94 mmol) in ethanol (20 mL) was added 10% Pd-C (0.1 g). The mixture was stirred at 25 C. for 12 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give compound 48-a (310 mg, yield: 82%), which was used directly for the next step without purification.
	With hydrogen;5% Pd(II)/C(eggshell); at 18 - 25℃; under 760.051 Torr; for 3h;Product distribution / selectivity;	Intermediate 10; 2-Chloro-N-(l-methyl-lH-imidazol-4-v?-7-r(4-methylphenyl)sulfonyl1-7H-pyrrolor2.3- J1pyrimidin-4-aminel-Methyl-4-nitro-lH-imidazole (Intermediate 1, 50 mg, 0.39 mmol) was dissolved in ethanol (5 mL) and Pd/C (5 wt%, Degussa, 20.93 mg, 9.83 mumol) was added. The reaction mixture stirred under 1 atm of hydrogen at r.t. for 3 hours and was then filtered through diatomaceous earth (Celite brand) to give 1 -methyl- lH-imidazol-4-amine. 2,4-Dichloro-7-[(4- methylphenyl)sulfonyl]-7H-pyrrolo[2,3-<i]pyrimidine (Intermediate 9, 108 mg, 0.31 mmol) and TEA (0.110 mL, 0.79 mmol) was added to the reaction mixture. The reaction mixture was stirred at 1000C in a microwave reactor for 2hr. After completion of the reaction as indicated by TLC, the reaction mixture was evaporated in vacuo to obtain a light yellow solid, which was purified by column chromatography (3% MeOH, 0.3% NH4OH in DCM) to provide the title product (90 mg, 57%) as a white solid. LCMS: 403 [M+H]+.1U NMR (400 MHz, CHLOROFORM-D) delta ppm 8.92 (s, 1 H) 8.03 (d, J=8.34 Hz, 2 H) 7.41 (s, 1 H) 7.39 (d, J=3.79 Hz, 1 H) 7.25 (d, J=8.08 Hz, 2H) 6.48 (s, 1 H) 3.67 (s, 3 H) 2.33 (s, 3 H).
	With hydrogen;palladium on activated charcoal; In methanol;	Building block 6, a prime side amine (BB6)1 -Methyl-1 H-imidazol-4-amine (BB6)The title compound was achieved by catalytic hydrogenation in MeOH of 1 -methyl-4-nitro-1 H- imidazole using Pd/C as catalyst. Removal of the catalyst by filtration of the reaction mixture through Celite followed by evaporation of the solvent gave the title compound, which was used in the next step without further purification.
	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 6h;Inert atmosphere;	Synthesis of LXXI:To a stirred solution of compound LXX (4g, 31 mmol) in ethanol (20 mL) was added 1 0%Pd-C (catalytic) under nitrogen atmosphere. The reaction mixture was evacuated using high vacuum and stirred in presence of hydrogen gas at balloon pressure at room temperature for 6 h. The reaction mixture was filtered through a celite bed. The organic solvent was evaporated under reduced pressure to afford 1-methyl-1H-imidazol-4-amine (LXXI, 2.5g) MS (M+1) 98. The crude material was carried forward to next step without purification.
	With hydrogen;palladium on activated carbon; In ethanol; at 18 - 25℃; under 760.051 Torr; for 3h;	1 -Methyl-4-nitro- lH-imidazole (Intermediate 1, 500 mg, 3.93 mmol) was dissolved in ethanol (7.868 mL) and Pd/C (10 wt.%, Degussa, 105 mg, 0.10 mmol) was added. The reaction mixture was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered and the filtrate was cooled to 00C. 2,4,6-trichloro-l,3,5-triazine (580 mg, 3.15 mmol) and TEA (1.097 mL, 7.87 mmol) were then added. The reaction mixture was allowed to warm to 25C overnight. The reaction mixture was then filtered providing the title product as a tan solid (572 mg). LCMS: 246 [M+eta]+.
0.75 g	With palladium on activated charcoal; hydrogen; In ethanol; at 20℃; for 24h;	1-Methyl-4-nitroimidazole (1 g), Pd/C (0.1 g) and 20 ml of ethanol were exchanged in a balloon of hydrogen at room temperature for about 24 h.Vacuum filtration through celite, the filtrate was dried under reduced pressure to give the title product (0.75g).
	With palladium 10% on activated carbon; hydrogen; In methanol; at 25℃; under 775.743 Torr; for 1h;	To a solution of 1 -methyl-4-nitro-imidazole (2 g, 15.7 mmol, 1 eq.) in MeOH (100 ml) was added 10 % Pd/C (1 g, 15.7 mmol) under H2 . The mixture was stirred under H2 (15 psi) at 25 C for 1 h. The mixture was diluted with MeOH (50 ml) and filtered under reduced pressure. The filtrate was evaporated to give the title compound as a yellow oil. NMR (400 MHz, CDCl3) d = 7.03 (s, 1H), 6.17 (s, 1H), 3.60 - 3.10 (m, 5H).
0.75 g	With palladium on activated charcoal; hydrogen; In ethanol; at 10 - 35℃; for 24h;	Mix <strong>[3034-41-1]<strong>[3034-41-1]1-methyl-4-nitroimidazol</strong>e</strong> (1g), Pd / C (0.1g) and 20ml ethanol,Replace the air with a hydrogen balloon,The reaction was carried out at room temperature for about 24 h.The celite was suction-filtered under reduced pressure, and the filtrate was dried under reduced pressure to obtain the title product (0.75 g).

Reference： [1]Patent: EP2773638,2015,B1 .Location in patent: Paragraph 1084; 1086
[2]Patent: WO2012/30944,2012,A2 .Location in patent: Page/Page column 103
[3]Patent: US2012/53174,2012,A1 .Location in patent: Page/Page column 57
[4]Patent: WO2015/89337,2015,A1 .Location in patent: Paragraph 0280
[5]Patent: US2015/336982,2015,A1 .Location in patent: Paragraph 0329; 0330
[6]Acta Chemica Scandinavica,1990,vol. 44,p. 67 - 74
[7]Heterocycles,1996,vol. 42,p. 213 - 218
[8]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5703 - 5707
[9]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 69
[10]Patent: WO2012/172473,2012,A1 .Location in patent: Page/Page column 28
[11]Patent: WO2015/97121,2015,A1 .Location in patent: Page/Page column 136; 137
[12]Patent: WO2009/150462,2009,A1 .Location in patent: Page/Page column 68
[13]Patent: CN109678803,2019,A .Location in patent: Paragraph 0202-0207
[14]Patent: WO2019/121691,2019,A1 .Location in patent: Paragraph 0857
[15]Patent: CN110330484,2019,A .Location in patent: Paragraph 0076; 0086; 0087; 0089; 0090

11
[ 553-90-2 ]
[ 3034-38-6 ]
[ 3034-41-1 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 6113 - 6124
[2]Tetrahedron,1990,vol. 46,p. 6113 - 6124

12
[ 553-90-2 ]
[ 3034-38-6 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 1957 - 1960

13
[ 3034-38-6 ]
[ 616-38-6 ]
[ 3034-41-1 ]

Reference： [1]Liebigs Annalen der Chemie,1987,p. 77 - 80

14
[ 3034-41-1 ]
[ 67-66-3 ]
[ 161091-88-9 ]

Reference： [1]Polish Journal of Chemistry,1994,vol. 68,p. 2237 - 2248

15
[ 3034-41-1 ]
[ 107-59-5 ]
tert-butyl 1-methyl-4-nitroimidazol-5-ylacetate [ No CAS ]

Reference： [1]Polish Journal of Chemistry,1994,vol. 68,p. 2237 - 2248

16
[ 3034-41-1 ]
[ 107-14-2 ]
1-methyl-4-nitroimidazol-5-ylacetonitrile [ No CAS ]

Reference： [1]Polish Journal of Chemistry,1994,vol. 68,p. 2237 - 2248

17
[ 3034-41-1 ]
1-Methyl-imidazolidin-4-one oxime [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 9541 - 9552

18
[ 584-13-4 ]
[ 67-56-1 ]
[ 3034-41-1 ]
N,O-dimethyl-N'-(1,2,4-triazol-4-yl)isourea [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1996,vol. 32,p. 1040 - 1046

19
[ 212248-40-3 ]
[ 74-88-4 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1]Russian Journal of Organic Chemistry,1997,vol. 33,p. 1764 - 1766

20
[ 3034-41-1 ]
[ 4531-54-8 ]

Reference： [1]Russian Journal of General Chemistry,2002,vol. 72,p. 449 - 455
[2]Tetrahedron Letters,2002,vol. 43,p. 6613 - 6616
[3]Journal of Organic Chemistry,1998,vol. 63,p. 4878 - 4888

23
1-methyl-4-nitro-imidazole-carboxylic acid-⁽⁵⁾ [ No CAS ]
[ 3034-41-1 ]

Reference： [1]Helvetica Chimica Acta,1924,vol. 7,p. 714

24
1-methyl-4-nitro-imidazole-sulfonic acid-⁽⁵⁾ [ No CAS ]
[ 3034-41-1 ]

Reference： [1]Journal of the Chemical Society,1924,vol. 125,p. 1569

25
[ 7647-01-0 ]
[ 5413-88-7 ]
[ 3034-41-1 ]

Reference： [1]Helvetica Chimica Acta,1924,vol. 7,p. 714

26
[ 74-88-4 ]
silver-salt of 4-nitro-1⁽³⁾-imidazole [ No CAS ]
[ 3034-41-1 ]

Reference： [1]Journal of the Chemical Society,vol. 232,p. 235

27
[ 616-47-7 ]
HNO₃+H₂SO₄ [ No CAS ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1]Journal of the Chemical Society,1924,vol. 125,p. 1434

28
[ 7647-01-0 ]
[ 3034-41-1 ]
tin [ No CAS ]
[ 107-97-1 ]
[ 7664-41-7 ]
[ 74-89-5 ]

Reference： [1]Helvetica Chimica Acta,1924,vol. 7,p. 714

29
[ 616-47-7 ]
[ 3034-41-1 ]
[ 5213-50-3 ]
[ 19183-20-1 ]
[ 1671-82-5 ]

Yield	Reaction Conditions	Operation in experiment
< 1%	With sulfuric acid; sulfur trioxide; nitric acid; at 110 - 120℃; for 2h;Product distribution / selectivity;	Nitration of 1-methylimidazole with Nitric Acid and Sulfuric Acid Fuming nitric acid (1.5 ml, excess, d.1.544 g/ml) was added to 1-methylimidazole (100 mg, 1.22 mmol) at room temperature with stirring. Then sulfuric acid (1.5 ml, excess, fuming 30% SO3) was added slowly from the top of condenser. After addition, the reaction mixture was heated to 110 C. and then the reaction temperature was maintained between 110-120 C. for 2.0 hrs. The reaction mixture was cooled to room temperature and the resulting mixture of products was extracted with methylene chloride and the organic phase was dried with Na2SO4/NaHCO3. Evaporation of the solvent gave 61 mg of oil. Proton NMR showed that the ratio of the products was 7:25:45:2:1 (corresponding to 1-methyl-4-nitroimidazole, 1-methyl-2-nitroimidazole, 1-methyl-4,5-dinitroimidazole, 1-methyl-2,4-dinitroimidazole, and 1-methyl-2,4,5-trinitroimidazole). The yield of 1-methyl-2,4,5-trinitroimidazole is less then 1% based on the integration of the NMR.

Reference： [1]Patent: US7304164,2007,B1 .Location in patent: Page/Page column 7

30
[ 3034-41-1 ]
[ 72904-46-2 ]
[ 120721-86-0 ]

Reference： [1]Canadian Journal of Chemistry,1989,vol. 67,p. 508 - 516

31
[ 3034-41-1 ]
[ 132882-85-0 ]
RuCl₂(tmso)2(NMe-4-NO₂Im)2 [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1989,vol. 67,p. 508 - 516

32
[ 3034-41-1 ]
[ 194497-67-1 ]
[ 114384-14-4 ]

Reference： [1]Canadian Journal of Chemistry,1988,vol. 66,p. 117 - 122

33
[ 60314-39-8 ]
[ 3034-41-1 ]
[ 136537-80-9 ]

Reference： [1]Inorganic Chemistry,1991,vol. 30,p. 4374 - 4380

34
[ 3034-41-1 ]
[ 7205-98-3 ]
[ 100-00-5 ]
[ 89303-10-6 ]
[ 116271-00-2 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 6108 - 6118

35
[ 3034-41-1 ]
[ 7205-98-3 ]
[ 350-46-9 ]
[ 89303-18-4 ]
[ 116271-00-2 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 6108 - 6118

36
[ 3034-38-6 ]
[ 74-88-4 ]
[ 3034-41-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In acetonitrile; at 60℃;	Example 268a 1-Methyl-4-nitro-1H-imidazole 268a To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.5 mmol) in acetonitrile (20 mL) was added iodomethane (1.3 mL, 3.0 g, 21.2 mmol) dropwise while stirring at room temperature. The resulting mixture was stirred at 60C overnight. It was then evaporated under reduced pressure and the residue was diluted with water (20 mL). The mixture was extracted with dichloromethane (2 X 20 mL). The combined extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 268a as a yellow solid (1.8 g, 82%). MS-ESI: [M+H]+ 128.1. 1H NMR (500 MHz, DMSO-d6) delta 8.37 (s, 1H), 7.82 (s, 1H), 3.76 (s, 3H).
71%	With potassium carbonate; In acetonitrile; at 0 - 95℃; for 3h;	Synthesis of LXX:To stirred solution of 4-nitro-1H-imidazole (LXIX, 5g: 44 mmol) in acetonitrile (20 mL) was added K2C03 (18.2 g, 137 mmol) at 0C, followed by addition of methyl iodide (8.9 mL, 57mmol). The reaction mixture was heated at 95C for 3h. The reaction mixture was concentrated, filtered through a celite bed and diluted with water. The aqueous layer was extracted with chloroform and the separated organic layer was washed with brine solution and dried over anhydrous Na2SO4 before being filtered and evaporated under reduced pressure to afford 1-methyl-4-nitro-1H-imidazole (LXX, 4g, 71%). ?H NMR (400 MHz, DMSO-d6) oe 8.35 (s, 1H), 7.8 (s, 1H), 3.74 (s, 3H). MS (M+1): 128.
70%	With potassium carbonate; In acetonitrile; at 65℃; for 20h;	Intermediate P2: 1 -Methyl-4-nitro-1H-imidazole To the mixture of 4-nitro-1H-imidazole (3.00 g, 17.7 mmol), potassium carbonate (3.67 g, 26.5 mmol) and acetonitrile (20 mL) iodomethane (1 .32 mL, 21.2 mmol) was added during 10 minutes. The reaction mixture was stirred while heating at 65 C for 20 hours, cooled to room temperature and filtered through the sintered glass funnel. Filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent: chloroform/methanol 98:2 to 90: 10, v/v) to obtain an amorphous, creamy solid. The solid was hot-crystallized from isopropanol to obtain after filtration and drying title product in the form of light-creamy crystals with the yield of 70% (1.58 g, 12.4 mmol). Melting point 134.7-135.3C. 1H NMR (500 MHz, CDCl3) delta 7.79 (d, J=1 ,4 Hz, 1 H), 7.44 (s, 1 H), 3.84 (s, 3H). 13C NMR (125 MHz, CDCI3) delta 148.1 , 136.7, 120.3, 34.60.

46%	With potassium carbonate; In acetonitrile; at 60℃;Sealed vial;	Step B: To a mixture of 4-nitro-lH-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.6 mmol) in acetonitrile (18 mL) was added iodomethane (1.32 mL, 21.2 mmol). The mixture was heated at 60 C in a sealed vial overnight. The mixture was filtered and the filter cake washed with acetone. The filtrate was concentrated under reduced pressure, the residue was diluted with hot propan-2-ol, cooled, and then filtered. The obtained solid was dissolved in chloroform, filtered, and the filtrate concentrated under reduced pressure. The residue was triturated with propan-2-ol and filtered to afford l-methyl-4-nitro-lH-imidazole (1.03 g, 46%) as a tan solid. 1H NMR (300 MHz, DMSO-t/6) delta 8.37 (d, J= 1.1 Hz, 1H), 7.82 (s, 1H), 3.76 (s, 3H).
46%	With potassium carbonate; In acetonitrile; at 60℃;Sealed vial;	Example 20Preparation of 3-(4-fluorophenylsulfonyl)-N-Q-methyl-lH-imidazol-4- vDisoq uinolin- 1-amine[00277] Step A: To a mixture of 4-nitro-lH-imidazole (2.0 g, 17.7 mmol) andK2CO3 (3.67 g, 26.6 mmol) in acetonitrile (18 mL) was added iodomethane (1.32 mL, 21.2 mmol) and the mixture was heated in a sealed vial at 60 C overnight. The mixture was filtered washing with acetone. The filtrate was concentrated under reduced pressure, and the residue was diluted with hot isopropanol and cooled, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform and filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with propan-2-ol and collected by filtration to afford 1- methyl-4-nitro-lH-imidazole (1.03 g, 46%) as a tan solid. 1H NMR (300 MHz, DMSO-t/e) delta 8.37 (d, J= 1.1 Hz, 1H), 7.82 (s, 1H), 3.76 (s, 3H).
46%	With potassium carbonate; In acetonitrile; at 60℃;	Step A: To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.6 mmol) in acetonitrile (18 mL) was added iodomethane (1.32 mL, 21.2 mmol) and the mixture was heated in a sealed vial at 60 C. overnight. The mixture was filtered washing with acetone. The filtrate was concentrated under reduced pressure, and the residue was diluted with hot isopropanol and cooled, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform and filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with propan-2-ol and collected by filtration to afford 1-methyl-4-nitro-1H-imidazole (1.03 g, 46%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) delta 8.37 (d, J=1.1 Hz, 1H), 7.82 (s, 1H), 3.76 (s, 3H).
	With potassium carbonate; In acetonitrile; at 65℃;	4-Nitro-lH-imidazole (2 g, 17.69 mmol) was dissolved in acetonitrile (20 mL) and potassium carbonate (3.67 g, 26.53 mmol) and iodomethane (1.327 mL, 21.22 mmol) were added. The reaction mixture was then heated at 650C overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo leaving a reddish orange solid (3.214 g). This material was purified utilizing ISCO (0-10% MeOEta/DCM). Concentration of the fractions in vacuo provided the title compound as a yellow solid (2.071 g). The title compound was re-crystalized out of isopropanol leaving an off-white solid (1.564 g). LCMS: 128 [M+H]+.
	With potassium carbonate; In acetonitrile; at 65℃;	Intermediate 1; 1 -Methyl-4-nitro- lH-imidazole4-Nitro-lH-imidazole (2 g, 17.69 mmol) was dissolved in acetonitrile (20 niL) and potassium carbonate (3.67 g, 26.53 mmol) and iodomethane (1.327 mL, 21.22 mmol) were added. The reaction mixture then heated at 650C overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo leaving a reddish orange solid (3.214 g). This material was purified by ISCO (0-10% MeOEta/DCM). Concentration of the fractions in vacuo provided the title product as a yellow solid (2.071 g). The title product was re-crystalized out of isopropanol leaving an off- white solid (1.564 g). LCMS: 128 [M+Eta]+.
	With potassium carbonate; In acetonitrile; at 65℃;	4-Nitro- IH- imidazole (2 g, 17.69 mmol) was dissolved in acetonitrile (20 niL), and potassium carbonate (3.67 g, 26.53 mmol) and iodomethane (1.327 mL, 21.22 mmol) were added. The reaction mixture was then heated at 65C overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo leaving a reddish orange solid (3.214 g). This material was purified by ISCO (0-10% MeOeta/DCM). Concentration of the fractions in vacuo provided the title product as a yellow solid (2.058 g)-LCMS: 128 [M+eta]+.
1.5 g	With potassium carbonate; In acetonitrile; for 12h;Reflux;	4-Nitroimidazole (1.41 g), potassium carbonate (2.5 g), iodomethane (1.9 g) and 20 mL of acetonitrile were refluxed for 12 h.Dry under reduced pressure, add 50 mL of water, and extract three times with 50 mL of ethyl acetate.The organic layers were combined, washed with saturated aqueous sodium chloride solution, the organic phase was dried over anhydrous Na2SO4 was added,Drying under reduced pressure gave 1-methyl-4-nitroimidazole (1.5 g).
	With potassium carbonate; In acetonitrile; at 60℃; for 14h;	To a solution of 4-nitro- 1 H-imidazole (5.0 g, 44 mmol, 1 eq.) in ACN (50 ml) was added K2C03 (9.17 g, 66 mmol). Methyl iodide (7.53 g, 53 mmol, 3.30 ml) was added slowly to the mixture at rt, then the mixture was warmed to 60 C for 14 h. The solvent was removed under reduced pressure, then the residue was diluted with water (30 ml), extracted with DCM (5 x 30 ml) and the combined organic layers dried over Na2S04. The organic phase was concentrated in vacuo to give the title compound as a yellow solid. 'H NMR (400 MHz, DMSO-de) d = 8.35 (s, 1H), 7.80 (s, 1H), 3.75 (s, 3H).
1.5 g	With potassium carbonate; In acetonitrile; for 12h;Reflux;	4-nitroimidazole(1.41 g), potassium carbonate (2.5 g), methyl iodide (1.9 g), and 20 mL of acetonitrile,The reaction was refluxed for 12 h. Spin dry under reduced pressure, add 50mL of water,It was extracted three times with 50 mL of ethyl acetate. The organic layers were combined and washed with saturated brine.The organic phase was dried by adding anhydrous Na2SO4, and dried under reduced pressure.1-methyl-4-nitroimidazole(1.5g).

Reference： [1]Patent: EP2773638,2015,B1 .Location in patent: Paragraph 1084; 1085
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 144 - 158
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 265 - 285
[4]Patent: WO2015/97121,2015,A1 .Location in patent: Page/Page column 136; 137
[5]Patent: WO2014/20531,2014,A1 .Location in patent: Page/Page column 14-15
[6]Patent: WO2012/30914,2012,A1 .Location in patent: Page/Page column 77
[7]Patent: WO2012/30944,2012,A2 .Location in patent: Page/Page column 103
[8]Patent: US2012/53174,2012,A1 .Location in patent: Page/Page column 57
[9]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 57-58
[10]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 64
[11]Patent: WO2009/150462,2009,A1 .Location in patent: Page/Page column 68
[12]Patent: CN109678803,2019,A .Location in patent: Paragraph 0202; 0205
[13]Patent: WO2019/121691,2019,A1 .Location in patent: Paragraph 0856
[14]Patent: CN110330484,2019,A .Location in patent: Paragraph 0086; 0088

37
[ 3034-41-1 ]
[ 6693-08-9 ]
[ 1208893-82-6 ]

Yield	Reaction Conditions	Operation in experiment
		2,6-Dichloro-5-fluoro-Lambda/-(l-methyl-lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 500 mg, 3.93 mmol) was dissolved in ethanol (6.771 mL) and Pd/C (10 wt%, Degussa, 105 mg, 0.10 mmol) was added. The reaction was subjected to 1 atm of hydrogen for 3 hours. TLC indicated that the reaction was completed, and the reaction mixture was filtered through Celite. The filtrate was cooled to 00C and TEA (1.097 mL, 7.87 mmol) and <strong>[6693-08-9]2,4,6-trichloro-5-fluoropyrimidine</strong> (obtained via the procedure described in PCT Pub. No. WO2008/132502, 792 mg, 3.93 mmol) were added. The reaction was allowed to warm to room temperature slowly overnight. The reaction mixture was filtered providing the title compound as a yellow solid (820 mg) with 95% purity. LCMS: 263 [M+Eta]+.

Reference： [1]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 67

38
[ 3034-41-1 ]
[ 5750-76-5 ]
[ 1208893-78-0 ]

Yield	Reaction Conditions	Operation in experiment
		2, 5-Dichloro-Lambda/-(l -methyl- lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 500 mg, 3.93 mmol) was dissolved in ethanol (7.868 mL) and Pd/C (10 wt%, Degussa, 105 mg, 0.10 mmol) was added. The reaction mixture was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and 2,4,5-trichloropyrimidine (0.361 mL, 3.15 mmol) and TEA (1.097 mL, 7.87 mmol) were added. The reaction mixture was stirred overnight at rt. The reaction mixture was filtered providing the title compound as a pale yellow solid (538 mg). LCMS: 245 [M+Eta]+.

Reference： [1]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 66

39
[ 3764-01-0 ]
[ 3034-41-1 ]
[ 1208893-80-4 ]

Yield	Reaction Conditions	Operation in experiment
		2, 6-Dichloro-Lambda/-(l -methyl- lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lEta-imidazole (Intermediate 5, 1.0 g, 7.87 mmol) was dissolved in ethanol (12.82 ml) and Pd/C (10 wt%, Degussa, 0.209 g, 0.20 mmol) was added. The reaction was subjected to 1 atm of hydrogen for 3 hours. TLC analysis indicated that the reaction was completed and the reaction mixture was filtered through Celite and cooled to 00C. TEA (2.193 ml, 15.74 mmol) and 2,4,6-trichloropyrimidine (0.722 ml, 6.29 mmol) were added and the reaction was allowed to slowly warm to rt overnight. LCMS confirmed formation of the desired product. The reaction mixture was then filtered leaving a tan solid (1.526 g) which was confirmed by LCMS to be the title compound with 99% purity. The material was used in a subsequent step without any further purification. LCMS: 245 [M+H]+.

Reference： [1]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 66-67

40
[ 3034-41-1 ]
[ 19646-07-2 ]
[ 1208893-84-8 ]

Yield	Reaction Conditions	Operation in experiment
		2-Chloro-5-methoxy-N-(l-methyl-lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 400 mg, 3.15 mmol) was dissolved in ethanol (4.063 mL) and Pd/C (10 wt%, Degussa, 84 mg, 0.08 mmol) was added. The reaction was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and TEA (0.877 mL, 6.29 mmol) and 2,4-dichloro-5-methoxypyrimidine (563 mg, 3.15 mmol) were added. The reaction was subsequently heated to reflux overnight. The volatiles were concentrated in vacuo leaving a rust solid (1.140 g). This material was purified utilizing ISCO (0-10% MeOEta/DCM). Concentration of the fractions in vacuo provided the title compound as a yellow solid (603 mg). LCMS: 240 [M+Eta]+.

Reference： [1]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 67

41
[ 870065-73-9 ]
[ 3034-41-1 ]
[ 1208893-79-1 ]

Yield	Reaction Conditions	Operation in experiment
		,5-Difluoro-6-[(l-methyl-lH-imidazol-4-yl)aminolnicotinonitrile l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 500 mg, 3.93 mmol) was dissolved in ethanol (7.868 mL) and Pd/C (10 wt%, Degussa, 105 mg, 0.10 mmol) was added. The reaction mixture was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and the filtrate was cooled to O0C. <strong>[870065-73-9]2,5,6-trifluoronicotinonitrile</strong> (497 mg, 3.15 mmol) and TEA (1.097 mL, 7.87 mmol) were added and the reaction mixture was allowed to warm to rt slowly overnight. The reaction mixture was filtered providing the title compound as a yellow solid (566 mg). LCMS: 236 [M+Eta]+.

Reference： [1]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 66

42
[ 3034-41-1 ]
[ 2927-71-1 ]
[ 1208893-88-2 ]

Yield	Reaction Conditions	Operation in experiment
		2-Chloro-5-fluoro-Lambda/-(l -methyl- lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 400 mg, 3.15 mmol) was dissolved in ethanol (4.063 mL) and Pd/C (10 wt%, Degussa, 84 mg, 0.08 mmol) was added. The reaction was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and TEA (0.877 mL, 6.29 mmol) and 2,4-dichloro-5-fluoropyrimidine (525 mg, 3.15 mmol) were added. The reaction was stirred at rt overnight. The reaction mixture was filtered providing the title compound as a white solid (495 mg). LCMS: 228 [M+Eta]+.

Reference： [1]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 68

43
[ 1780-31-0 ]
[ 3034-41-1 ]
[ 1208893-87-1 ]

Yield	Reaction Conditions	Operation in experiment
		2-Chloro-5-methyl-N-(l-methyl-lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 400 mg, 3.15 mmol) was dissolved in ethanol (4.063 mL) and Pd/C (10 wt%, Degussa, 84 mg, 0.08 mmol) was added. The reaction was subjected to 1 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and TEA (0.877 mL, 6.29 mmol) and 2,4-dichloro-5-methylpyrimidine (0.369 mL, 3.15 mmol) were added. The reaction was heated to reflux overnight. The reaction was subsequently heated to reflux overnight. The volatiles were concentrated in vacuo leaving a rust solid (1.207 g). This material was purified utilizing ISCO (0-10% MeOEta/DCM). Concentration of the fractions in vacuo provided the title compound as a yellow solid (542 mg). LCMS: 224 [M+Eta]+.

Reference： [1]Patent: WO2010/20810,2010,A1 .Location in patent: Page/Page column 67-68

44
[ 19182-81-1 ]
[ 74-89-5 ]
[ 3034-41-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5703 - 5707

46
[ 616-47-7 ]
[ 3034-41-1 ]
[ 3034-42-2 ]
[ 19183-15-4 ]

Reference： [1]Synthesis,2011,p. 2859 - 2864

47
[ 3034-41-1 ]
[ 19183-20-1 ]
[ 19183-15-4 ]

Reference： [1]Synthesis,2011,p. 2859 - 2864
[2]Synthesis,2011,p. 2859 - 2864

48
[ 3034-41-1 ]
[ 1241914-72-6 ]
[ 1362909-87-2 ]

Yield	Reaction Conditions	Operation in experiment
		Step C: To l-methyl-4-nitro-lH-imidazole from Step B (80 mg, 0.63 mmol) in EtOH (5 mL) was added 10% Pd-C (30 mg) and the mixture was stirred under a hydrogen atmosphere for 0.5 h. The mixture was filtered and concentrated under reduced pressure. To the residue were added DMF (3 mL), TEA (0.1 mL, 0.7 mmol), and KI (20 mg, 0.12 mmol) followed by (4-chloroquinazolin-2-yl)(4- fluorophenyl)methanone from Step A (100 mg, 0.35 mmol). The mixture was stirred overnight at rt and concentrated under reduced pressure. The residue is purified by chromatography to afford (4-fluorophenyl)(4-(l -methyl- lH-imidazol-4- ylamino)quinazolin-2-yl)methanone.

Reference： [1]Patent: WO2012/30914,2012,A1 .Location in patent: Page/Page column 77-78

49
[ 3034-41-1 ]
[ 20485-39-6 ]
[ 1387556-73-1 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 6158 - 6162
[2]Journal of Organic Chemistry,2012,vol. 77,p. 7677 - 7683

50
[ 3034-41-1 ]
[ 89088-69-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 144 - 158
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 265 - 285

51
[ 3034-41-1 ]
[ 39971-65-8 ]
1-methyl-4-nitro-5-(trifluoromethyl)-1H-imidazole [ No CAS ]
1-methyl-2-(trifluoromethyl)-4-nitro-1H-imidazole [ No CAS ]

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

52
[ 3034-41-1 ]
bis(((difluoromethyl)sulfinyl)oxy)zinc [ No CAS ]
5-(difluoromethyl)-1-methyl-4-nitro-1H-imidazole [ No CAS ]

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

53
[ 3034-41-1 ]
4-(5-chloro-3-(4-chloro-2-fluorobenzyl)-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)morpholine [ No CAS ]
3-(4-chloro-2-fluorobenzyl)-2-methyl-N-(1-methyl-1H-imidazol-4-yl)-7-morpholinopyrazolo[1,5-a]pyrimidin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%		To the suspension of <strong>[3034-41-1]1-methyl-4-nitro-1H-imidazole</strong> (128 mg, 1.012 mmol) in ethanol (5 mL) 5% palladium on carbon (10 mg, 0.053 mmol) was added. The reaction mixture was degassed under reduced pressure and stirred under hydrogen atmosphere at roomtemperature for 3 hours. The reaction mixture was filtered over celite layer and washed with ethanol. The filtrate was concentrated under reduced pressure, dissolved in toluene, transferred to a Schlenk flask and again concentrated under reduced pressure. 4-(5-Chloro- 3 -(4-chloro-2-fluorobenzyl)-2-methylpyrazolo [1, 5-a]pirymidyn-7-yl)morpholine obtained in Example 1, Step F (200 mg, 0.506 mmol), tris(dibenzylideneacetone)dipalladium(0)(23.2 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene (29,3 mg, 0,05 1 mmol) and sodium carbonate (107 mg, 1.012 mmol) were added and the mixture was degassed under reduced pressure. Under argon atmosphere degassed toluene (5 mL) was added and the mixture was purged with argon for 15 minutes. Reaction mixture was heated to 100 C for 24 hours. The mixture was cooled to room temperature, diluted with ethylacetate (10 mL), filtered through celite layer and washed with ethyl acetate (25 mL). The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silicagel, eluent: AcOEt 100% to AcOEt:methanol = 9:1, v/v). The product was hot-crystallized from AcOEt:heptan to obtain white crystals with a yield of 27% (63 mg, 0.138 mmol).

Reference： [1]Patent: WO2015/118434,2015,A1 .Location in patent: Page/Page column 35; 36

54
[ 616-47-7 ]
[ 3034-41-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium nitrate; In neat (no solvent); at 20℃; for 1h;Green chemistry;	General procedure: A mixture of aromatic compound (1 mmol), sodium nitrate(1 mmol) and SO3H-functionalized magnetic core/shell nanocatalyst (0.1 mmol) was pulverized in a mortar at room temperature for an appropriate time. The reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, CH2Cl2 (5.0 mL) was then added to the mixture and filtered. Evaporation of the solvent followed by recrystallization or column chromatography on silicagel of the crude product gave the corresponding nitratedcompounds in good to excellent yields. The nanocatalyst was simply separated from the reaction mixture by using anexternal magnet, washed with methanol/diluted HCl solutionand then dried in an oven at 60 C. Before reusing the recycled catalyst, it was weighted in any cycle, and after that, it was reused in subsequent runs. Furthermore, fresh catalyst was added to reciprocate decreased mass loss, if it was considerable.

Reference： [1]Journal of the Iranian Chemical Society,2017,vol. 14,p. 485 - 490

55
[ 3034-41-1 ]
[ 25554-84-1 ]
[ 20041-97-8 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1413 - 1416

56
[ 3034-41-1 ]
[ 25554-84-1 ]
[ 7464-68-8 ]
[ 20041-97-8 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1413 - 1416

57
[ 3034-41-1 ]
[ 104-15-4 ]
C₄H₅N₃O₂*C₇H₈O₃S [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 10774 - 10783

58
[ 3034-38-6 ]
[ 74-88-4 ]
[ 3034-41-1 ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 10774 - 10783

59
[ 3034-41-1 ]
1-methyl-4-nitro-1<i>H</i>-imidazole; hydrochloride [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 10774 - 10783

60
[ 616-47-7 ]
[ 3034-41-1 ]
[ 19183-15-4 ]

Yield	Reaction Conditions	Operation in experiment
13.9%Chromat.; 35.2%Chromat.	With sulfuric acid; sulfur trioxide; nitric acid; at 15 - 80℃; for 2.5h;	General procedure: HNO3 (98%, 6 ml) was added dropwise to H2SO4 (15% SO3 in H2SO4, 18 ml) while maintaining the temperature below 15C. After the addition was complete, the mixture was stirred for additional 15 min. 1-Methylimidazole (5) (1.64 g, 0.02 mol) was then added dropwise carefully. The addition rate was maintained such that the internal reaction temperaturere mained below 15C. After completion of the addition, the mixture was heated gradually to 80C, stirred for 2.5 h, cooled to room temperature, and poured onto crushed ice (100 g). The mixture was extracted with CH2Cl2 (5×50 ml). The extracts were combined, washed with H2O, dried over Na2SO4, and evaporated under reduced pressure. Mixture of 1-methyl-4-nitroimidazole (6), 1-methyl-4,5-dinitroimidazole (8), and 1-methyl-2,4,5-trinitroimidazole (MTNI). Yield 1.65 g, pale-yellow powder. HPLC analysis showed that the molar ratio of the products was 2:14:35 (corresponding to MTNI, compounds 6 and 8, respectively). The unisolated yield of MTNI was 2%.

Reference： [1]Chemistry of Heterocyclic Compounds,2020,vol. 56,p. 55 - 59
Khim. Geterotsikl. Soedin.,2020,vol. 56,p. 55 - 59,5

61
[ 3034-41-1 ]
[ 19183-15-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sulfuric acid; sulfur trioxide; nitric acid; at 15 - 120℃; for 2.5h;	General procedure: HNO3 (98%, 6 ml) was added dropwise to H2SO4 (15% SO3 in H2SO4, 18 ml) while maintaining the temperature below 15C. After the addition was complete, the mixture was stirred for additional 15 min. 1-Methylimidazole (5) (1.64 g, 0.02 mol) was then added dropwise carefully. The addition rate was maintained such that the internal reaction temperaturere mained below 15C. After completion of the addition, the mixture was heated gradually to 80C, stirred for 2.5 h, cooled to room temperature, and poured onto crushed ice (100 g). The mixture was extracted with CH2Cl2 (5×50 ml). The extracts were combined, washed with H2O, dried over Na2SO4, and evaporated under reduced pressure. Mixture of <strong>[3034-41-1]<strong>[3034-41-1]1-methyl-4-nitroimidazol</strong>e</strong> (6), 1-methyl-4,5-dinitroimidazole (8), and 1-methyl-2,4,5-trinitroimidazole (MTNI). Yield 1.65 g, pale-yellow powder. HPLC analysis showed that the molar ratio of the products was 2:14:35 (corresponding to MTNI, compounds 6 and 8, respectively). The unisolated yield of MTNI was 2%.

Reference： [1]Chemistry of Heterocyclic Compounds,2020,vol. 56,p. 55 - 59
Khim. Geterotsikl. Soedin.,2020,vol. 56,p. 55 - 59,5

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 3034-41-1 ]

Nitroes

[ 4897-25-0 ]

5-Chloro-1-methyl-4-nitroimidazole

Similarity: 0.82

[ 3034-42-2 ]

1-Methyl-5-nitroimidazole

Similarity: 0.80

[ 57531-38-1 ]

5-Chloro-4-nitro-1H-imidazole

Similarity: 0.78

[ 6963-65-1 ]

4-Bromo-5-nitroimidazole

Similarity: 0.77

[ 3034-38-6 ]

5-Nitro-1H-imidazole

Similarity: 0.76

Related Parent Nucleus of
[ 3034-41-1 ]

Imidazoles

[ 4897-25-0 ]

5-Chloro-1-methyl-4-nitroimidazole

Similarity: 0.82

[ 3034-42-2 ]

1-Methyl-5-nitroimidazole

Similarity: 0.80

[ 57531-38-1 ]

5-Chloro-4-nitro-1H-imidazole

Similarity: 0.78

[ 6963-65-1 ]

4-Bromo-5-nitroimidazole

Similarity: 0.77

[ 3034-38-6 ]

5-Nitro-1H-imidazole

Similarity: 0.76

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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.
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

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. 3034-41-1 ]

Quality Control of [ 3034-41-1 ]

Related Doc. of [ 3034-41-1 ]

Product Details of [ 3034-41-1 ]

Calculated chemistry of [ 3034-41-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3034-41-1 ]

Application In Synthesis of [ 3034-41-1 ]

[ 3034-41-1 ] Synthesis Path-Upstream 1~9

[ 3034-41-1 ] Synthesis Path-Downstream 1~61

Related Functional Groups of [ 3034-41-1 ]

Nitroes

Related Parent Nucleus of [ 3034-41-1 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3034-41-1 ]

Related Parent Nucleus of
[ 3034-41-1 ]