[ CAS No. 169770-25-6 ] {[proInfo.proName]}

Name: 169770-25-6|Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate|98%
Brand: Ambeed
SKU: A145349
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Quality Control of [ 169770-25-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 169770-25-6 ]

SDS Specification

Alternatived Products of [ 169770-25-6 ]

Product Details of [ 169770-25-6 ]

CAS No. :	169770-25-6	MDL No. :	MFCD08275078
Formula :	C₆H₇N₃O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FZSWXFKGZZOIMM-UHFFFAOYSA-N
M.W :	185.14	Pubchem ID :	11286874
Synonyms :

Calculated chemistry of [ 169770-25-6 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.59
TPSA :	89.94 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) :	-7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.04
Log Po/w (XLOGP3) :	0.36
Log Po/w (WLOGP) :	0.11
Log Po/w (MLOGP) :	-1.0
Log Po/w (SILICOS-IT) :	-1.88
Consensus Log Po/w :	-0.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.3
Solubility :	9.25 mg/ml ; 0.05 mol/l
Class :	Very soluble
Log S (Ali) :	-1.81
Solubility :	2.84 mg/ml ; 0.0154 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.26
Solubility :	103.0 mg/ml ; 0.555 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.42

Safety of [ 169770-25-6 ]

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

Application In Synthesis of [ 169770-25-6 ]

* 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 [ 169770-25-6 ]
Downstream synthetic route of [ 169770-25-6 ]

[ 169770-25-6 ] Synthesis Path-Upstream 1~5

1
[ 169770-25-6 ]
[ 128293-64-1 ]

Reference： [1] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 8151 - 8153

2
[ 169770-25-6 ]
[ 162085-97-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen In methanol; ethyl acetate for 14 h;	Methyl l-methyl-4- nitroimidazole-2-carboxylate 40 (3.3 g, 17.8 mmol), dissolved in 1 : 1 MeOH:EtOAc (100 niL), was shaken with hydrogen at 70 psi, for 14 h in presence of Pd/C (400 mg). The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as black oil. The residue was taken up in benzene and concentrated to furnish the amine as black solid, filtered and washed with ether (2.5 g, 88percent). The crude amine was dissolved in CH₃CN (50 mL) and DIEA (2.3, 18 mmol). A solution of 1- methyl-2-trichloroacetylimidazole 24 (3.6 g, 14.7 mmol) in CH₃CN (50 mL) was added to the amine solution at 0 ⁰C. The reaction mixture was allowed to stir for 10 h, solvent was removed and the residue was taken up in MeOH and the product was precipitated by addition Of Et₂O to furnish desired compound 41 (2.13 g, 68percent). ¹H- NMR (DMSO-d₆) δlψ.1 1 (s, exch, IH, NH), 7.69 (s, IH, Im'-C⁵H), 7.43 (s, IH, Im- C⁵H), 7.07 (s, IH, Im-C⁴H), 3.99 (s, 3H, CH₃), 3.97 (s, 3H, CH₃), 3.82 (s, 3H, OCH₃). ¹³C-NMR (75 MHz, DMSO-d₆) 6159.4 (+, s, CO), 157.2 (+, s, CO), 138.9 (+, s, Im- C²), 137.2 (+, s, Im-C²), 132.4 (+, s, Im-C⁴), 128.9 (-, d, Im-C⁴), 127.7 (-, d, Im-C⁵), 117.3 (-, d, Im-C⁵), 61.9 (+, t, -OCH₂-), 37.6 (-, q, CH₃), 35.8 (-, q, CH₃), 14.2 (-, q, CH₃). EI-HRMS: m/z calcd for C_{1 1}H₁₃N₅O₃ 263.1018; found 263.1016 (M⁺, 100percent), 204.0888 (27percent), 182.0573 (27percent), 150.0301 (30percent), 109.0393 (26percent).
88%	With hydrogen In methanol; ethyl acetate for 14 h;	Methyl-4-nitro-imidazole-2- carboxylate 40 (5 g, 27 mmol) was dissolved in 1 : 1 mixture of MeOH and EtOAc (150 mL). A slurry of moist 10percent PdVC in EtOAc was added and the contents were stirred vigorously under hydrogen (70 psi) for 14 h. The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as green solid. The crude amine without any further purification was taken up in CH₃CN (150 mL). Contents were cooled to 0 ⁰C and DIEA (6.9 mL, 37.7 mmol) was added. A solution of 1- methyl-4-nitro-2-trichloroacetylpyrrole 23 (7.6 g, 28.2 mmol) in CH₃CN (20 mL) was added and the reaction mixture was allowed to stir at ambient temperature for 14 h, EPO <DP n="90"/>during which solid precipitated out. The reaction mixture was filtered to furnish 42 as yellow solid (5 g, 60percent). The filtrate was concentrated and the residue was taken up in MeOH. Et₂O was added to furnish a second crop of 42 (1 g, 12percent). ¹H-NMR (DMSO-d₆) 611.14 (s, exch, IH, NH), 8.19 (d, IH, J = 1.2 Hz, Py-CH), 7.80 (d, IH, J = 1.2 Hz, Py-CH), 7.68 (s, IH, Im-CH), 3.96 (s, 3H, CH₃), 3.94 (s, 3H, CH₃), 3.82 (s, 3H, CH₃). ¹³C-NMR (75 MHz, DMSO-d₆) 6158.9 (+, s, CO), 157.4 (+, s, CO), 137.1 (+, s, Im-C²), 134.1 (+, s, Py-C⁴), 131.2 (+, s, Im-C²), 128.2 (-, d, Py-C⁵), 125.4 (+, s, Py-C²), 1 15.2 (-, d, Im-C⁵), 1 10.2 (-, d, Py-C³), 52.0 (-, q, OCH₃), 37.9 (-, q, CH₃), 35.2 (-, q, CH₃). EI-HRMS: m/z calcd for Ci₃Hi₅N₅O₅ 321.1073; found 321.1094 (M⁺, 20percent), 279.0997 (100percent), 194.0830 (72percent), 153.0317 (35percent).

Reference： [1] Patent: WO2007/45096, 2007, A1, . Location in patent: Page/Page column 87
[2] Patent: WO2007/45096, 2007, A1, . Location in patent: Page/Page column 87
[3] Heterocycles, 1995, vol. 41, # 6, p. 1181 - 1196
[4] Organic and biomolecular chemistry, 2003, vol. 1, # 15, p. 2630 - 2647

3
[ 67-56-1 ]
[ 120095-64-9 ]
[ 169770-25-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: at 40℃; for 0.166667 h; Stage #2: for 2 h;	MeOH (40 mL) was added to a sample of the trichloroacetyl compound 25, and the mixture stirred after heating to 40 ⁰C for 10 min. To ensure complete methanolysis, a small amount (100 mg) of NaH was added to the mixture. After stirring for 2 h, the resultant suspension was filtered to afford the title product (94percent yield). ¹H-NMR (CDCl₃) 67.84 (s, IH, Im-CH), 4.18 (s, 3H, CH₃), 3.93 (s, 3H, CH₃). EI-HRMS: m/z calcd for C₆H₇N₃O₄ 185.0437, found 185.0476 (100percent).

Reference： [1] Patent: WO2007/45096, 2007, A1, . Location in patent: Page/Page column 45; 86
[2] Heterocycles, 1995, vol. 41, # 6, p. 1181 - 1196
[3] Synthetic Communications, 2004, vol. 34, # 9, p. 1609 - 1615

4
[ 120095-64-9 ]
[ 124-41-4 ]
[ 169770-25-6 ]

Reference： [1] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 8151 - 8153

5
[ 30148-23-3 ]
[ 169770-25-6 ]

Reference： [1] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 8151 - 8153

[ 169770-25-6 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 120095-64-9 ]
[ 169770-25-6 ]

Yield	Reaction Conditions	Operation in experiment
94%		MeOH (40 mL) was added to a sample of the trichloroacetyl compound 25, and the mixture stirred after heating to 40 0C for 10 min. To ensure complete methanolysis, a small amount (100 mg) of NaH was added to the mixture. After stirring for 2 h, the resultant suspension was filtered to afford the title product (94% yield). 1H-NMR (CDCl3) 67.84 (s, IH, Im-CH), 4.18 (s, 3H, CH3), 3.93 (s, 3H, CH3). EI-HRMS: m/z calcd for C6H7N3O4 185.0437, found 185.0476 (100%).

Reference： [1]Organic Letters,2020,vol. 22,p. 533 - 536
[2]Patent: WO2007/45096,2007,A1 .Location in patent: Page/Page column 45; 86
[3]Heterocycles,1995,vol. 41,p. 1181 - 1196
[4]Synthetic Communications,2004,vol. 34,p. 1609 - 1615

2
[ 169770-25-6 ]
[ 162085-97-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen;palladium over charcoal; In methanol; ethyl acetate; under 3620.13 Torr; for 14h;Product distribution / selectivity;	Methyl l-methyl-4- nitroimidazole-2-carboxylate 40 (3.3 g, 17.8 mmol), dissolved in 1 : 1 MeOH:EtOAc (100 niL), was shaken with hydrogen at 70 psi, for 14 h in presence of Pd/C (400 mg). The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as black oil. The residue was taken up in benzene and concentrated to furnish the amine as black solid, filtered and washed with ether (2.5 g, 88%). The crude amine was dissolved in CH3CN (50 mL) and DIEA (2.3, 18 mmol). A solution of 1- methyl-2-trichloroacetylimidazole 24 (3.6 g, 14.7 mmol) in CH3CN (50 mL) was added to the amine solution at 0 0C. The reaction mixture was allowed to stir for 10 h, solvent was removed and the residue was taken up in MeOH and the product was precipitated by addition Of Et2O to furnish desired compound 41 (2.13 g, 68%). 1H- NMR (DMSO-d6) deltaltheta.1 1 (s, exch, IH, NH), 7.69 (s, IH, Im'-C5H), 7.43 (s, IH, Im- C5H), 7.07 (s, IH, Im-C4H), 3.99 (s, 3H, CH3), 3.97 (s, 3H, CH3), 3.82 (s, 3H, OCH3). 13C-NMR (75 MHz, DMSO-d6) 6159.4 (+, s, CO), 157.2 (+, s, CO), 138.9 (+, s, Im- C2), 137.2 (+, s, Im-C2), 132.4 (+, s, Im-C4), 128.9 (-, d, Im-C4), 127.7 (-, d, Im-C5), 117.3 (-, d, Im-C5), 61.9 (+, t, -OCH2-), 37.6 (-, q, CH3), 35.8 (-, q, CH3), 14.2 (-, q, CH3). EI-HRMS: m/z calcd for C1 1H13N5O3 263.1018; found 263.1016 (M+, 100%), 204.0888 (27%), 182.0573 (27%), 150.0301 (30%), 109.0393 (26%).
88%	With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; under 3620.13 Torr; for 14h;Product distribution / selectivity;	Methyl-4-nitro-imidazole-2- carboxylate 40 (5 g, 27 mmol) was dissolved in 1 : 1 mixture of MeOH and EtOAc (150 mL). A slurry of moist 10% PdVC in EtOAc was added and the contents were stirred vigorously under hydrogen (70 psi) for 14 h. The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as green solid. The crude amine without any further purification was taken up in CH3CN (150 mL). Contents were cooled to 0 0C and DIEA (6.9 mL, 37.7 mmol) was added. A solution of 1- methyl-4-nitro-2-trichloroacetylpyrrole 23 (7.6 g, 28.2 mmol) in CH3CN (20 mL) was added and the reaction mixture was allowed to stir at ambient temperature for 14 h, EPO <DP n="90"/>during which solid precipitated out. The reaction mixture was filtered to furnish 42 as yellow solid (5 g, 60%). The filtrate was concentrated and the residue was taken up in MeOH. Et2O was added to furnish a second crop of 42 (1 g, 12%). 1H-NMR (DMSO-d6) 611.14 (s, exch, IH, NH), 8.19 (d, IH, J = 1.2 Hz, Py-CH), 7.80 (d, IH, J = 1.2 Hz, Py-CH), 7.68 (s, IH, Im-CH), 3.96 (s, 3H, CH3), 3.94 (s, 3H, CH3), 3.82 (s, 3H, CH3). 13C-NMR (75 MHz, DMSO-d6) 6158.9 (+, s, CO), 157.4 (+, s, CO), 137.1 (+, s, Im-C2), 134.1 (+, s, Py-C4), 131.2 (+, s, Im-C2), 128.2 (-, d, Py-C5), 125.4 (+, s, Py-C2), 1 15.2 (-, d, Im-C5), 1 10.2 (-, d, Py-C3), 52.0 (-, q, OCH3), 37.9 (-, q, CH3), 35.2 (-, q, CH3). EI-HRMS: m/z calcd for Ci3Hi5N5O5 321.1073; found 321.1094 (M+, 20%), 279.0997 (100%), 194.0830 (72%), 153.0317 (35%).

Reference： [1]Organic Letters,2020,vol. 22,p. 533 - 536
[2]Patent: WO2007/45096,2007,A1 .Location in patent: Page/Page column 87
[3]Patent: WO2007/45096,2007,A1 .Location in patent: Page/Page column 87
[4]Heterocycles,1995,vol. 41,p. 1181 - 1196
[5]Organic and biomolecular chemistry,2003,vol. 1,p. 2630 - 2647

3
[ 71-44-3 ]
[ 169770-25-6 ]
N¹-(4'-nitro-1'-methylimidazole-2'-carboxyl)-1,12-diamino-4,9-diazadodecane [ No CAS ]
C₂₀H₃₂N₁₀O₆ [ No CAS ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 1609 - 1615

4
[ 24424-99-5 ]
[ 169770-25-6 ]
[ 500701-36-0 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8151 - 8153

5
[ 120095-64-9 ]
[ 124-41-4 ]
[ 169770-25-6 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8151 - 8153

6
[ 169770-25-6 ]
[ 128293-64-1 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8151 - 8153
[2]Organic Letters,2020,vol. 22,p. 533 - 536

7
[ 30148-23-3 ]
[ 169770-25-6 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8151 - 8153
[2]Organic Letters,2020,vol. 22,p. 533 - 536

8
[ 169770-25-6 ]
5-benzyloxy-7-[3-(2-carboxy-1-methyl-1H-imidazol-4-ylcarbamoyl)propionylamino]-1-chloromethyl-1,2-dihydrobenzo[e]indole-3-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Organic and biomolecular chemistry,2003,vol. 1,p. 2630 - 2647

9
[ 169770-25-6 ]
[ 633302-87-1 ]

Reference： [1]Organic and biomolecular chemistry,2003,vol. 1,p. 2630 - 2647

10
[ 169770-25-6 ]
methyl 4-butyrylamino-1-methyl-2-imidazolecarboxylate [ No CAS ]