128293-62-9|Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate| Ambeed

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Quality Control of [ 128293-62-9 ] Purity: 93% SDS Specification

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Product Details of [ 128293-62-9 ]

CAS No. :	128293-62-9
Formula :	C₇H₁₁N₃O₂
M.W :	169.18
SMILES Code :	O=C(C1=NC(N)=CN1C)OCC
MDL No. :	MFCD16036321

Safety of [ 128293-62-9 ]

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

Application In Synthesis of [ 128293-62-9 ]

* 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 [ 128293-62-9 ]

[ 128293-62-9 ] Synthesis Path-Downstream 1~41

1
[ 18595-34-1 ]
[ 128293-62-9 ]
[ 128293-63-0 ]

References: [1]Acta Chemica Scandinavica,1990,vol. 44,p. 67 - 74.

2
[ 24424-99-5 ]
[ 128293-62-9 ]
[ 128293-63-0 ]
[ 128293-69-6 ]

References: [1]Acta Chemica Scandinavica,1990,vol. 44,p. 67 - 74.

3
[ 128293-62-9 ]
[ 111333-97-2 ]
[ 128293-78-7 ]

References: [1]Acta Chemica Scandinavica,1990,vol. 44,p. 67 - 74.

4
[ 109012-23-9 ]
[ 128293-62-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;palladium 10% on activated carbon; In ethanol; ethyl acetate; under 836.056 Torr; for 3 - 4h;	Im-2 (0.4 g) in ETOH/ETHYL acetate (1: 1,14 mL) and Pd/C (10%, 0.3 g) were stirred under a slight positive pressure of hydrogen (ca 1.1 atm) for 3-4 hr. The reaction mixture was filtered using celite and solvent evaporated on the rotary. The remaining solid was freeze dried to yield a slightly yellow product. Yield (0.38 g, 95%). 1H NMR (DMSO): 8 6.45 (s, 1H), 4.5 (bs, 2H, NH2), 4.2 (q, 2H, J=7 Hz), 3.76 (s, 3H), 1.24 (t, 3H, J=7. 9 Hz).
	With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20℃; for 12h;	Ethyl 1-methyl-4-nitroimidazole-2-carboxylate17 (6, 613 mg, 3.1 mmol) was hydrogenated over 5% palladium on charcoal in ethanol. The resulting amino compound was dried thoroughly under vacuum to remove traces of ethanol. It was then dissolved in dichloromethane (20.0 mL) and the solution was cooled to 0-5 C. To the cold solution was added triethylamine (0.5 mL, 3.7 mmol) followed by benzoyl chloride (0.4 mL, 3.4 mmol). The reaction mixture was allowed to attain room temperature and then stirred for 12 h. Upon completion, the reaction was quenched with water (15.0 mL) and stirred for 15 min. The organic layer was separated and aqueous layer was washed with dichloromethane (2 × 10 mL). Combined organic layers were dried over sodium sulfate and evaporated to obtain a yellow oil. The crude product was purified by column chromatography using silica gel and 2% methanol in chloroform as the eluent system to obtain 7 as a yellow solid (808 mg, 96%).

References: [1]Acta Chemica Scandinavica,1990,vol. 44,p. 67 - 74.
[2]Patent: WO2006/89664,2006,A2 .Location in patent: Page/Page column 14; 30.
[3]Patent: WO2005/33077,2005,A1 .Location in patent: Page/Page column 54.
[4]Journal of the American Chemical Society,1992,vol. 114,p. 5911 - 5919.
[5]Journal of the American Chemical Society,1996,vol. 118,p. 6141 - 6146.
[6]Russian Journal of Bioorganic Chemistry,1998,vol. 24,p. 531 - 536.
[7]European Journal of Inorganic Chemistry,1999,p. 1557 - 1562.
[8]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 309 - 315.
[9]Tetrahedron Letters,2003,vol. 44,p. 1607 - 1610.
[10]Tetrahedron Letters,2002,vol. 43,p. 4295 - 4300.
[11]Tetrahedron,2005,vol. 61,p. 2493 - 2503.
[12]Journal of Organic Chemistry,2005,vol. 70,p. 10311 - 10322.
[13]Journal of Organic Chemistry,2000,vol. 65,p. 5506 - 5513.
[14]Synthetic Communications,2008,vol. 38,p. 33 - 44.
[15]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9145 - 9153.
[16]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 693 - 701.

5
[ 128293-62-9 ]
[ 28494-51-1 ]
[ 142211-80-1 ]

References: [1]Journal of the American Chemical Society,1992,vol. 114,p. 5911 - 5919.

6
[ 128293-62-9 ]
[ 77716-16-6 ]
[ 195387-59-8 ]

References: [1]Journal of the American Chemical Society,1996,vol. 118,p. 6141 - 6146.

7
[ 128293-62-9 ]
[ 515137-25-4 ]
[ 195387-60-1 ]

References: [1]Journal of the American Chemical Society,1996,vol. 118,p. 6141 - 6146.

8
[ 128293-62-9 ]
[4-tert-butyl-2-[5-tert-butyl-3-(5-tert-butyl-2-chlorocarbonylmethoxy-benzyl)-2-chlorocarbonylmethoxy-benzyl]-6-(5-tert-butyl-2-chlorocarbonylmethoxy-3-methyl-benzyl)-phenoxy]-acetyl chloride [ No CAS ]
C₈₀H₁₀₂N₁₂O₁₆ [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,1999,p. 1557 - 1562.

9
[ 128293-62-9 ]
[ 15944-88-4 ]
[ 288625-59-2 ]

References: [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 309 - 315.

10
[ 128293-62-9 ]
[ 120095-64-9 ]
1-methyl-4-[(1-methyl-4-nitro-1H-imidazole-2-carbonyl)-amino]-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5506 - 5513.

11
[ 128293-62-9 ]
[ 120122-47-6 ]
[ 142211-80-1 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5506 - 5513.

12
[ 128293-62-9 ]
BOCNH-X-CONH-X-OR; mixture of [ No CAS ]
4-BOCNH-X-CONH-X-CONH-1-methylimidazol-2-yl-COOR; mixture of [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2049 - 2057.

13
[ 128293-62-9 ]
[ 30148-23-3 ]
1-methyl-4-[(1-methyl-1H-imidazole-2-carbonyl)-amino]-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5506 - 5513.

14
[ 128293-62-9 ]
[ 107474-67-9 ]
[ 292070-77-0 ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

15
[ 128293-62-9 ]
[ 292069-98-8 ]
[ 292071-10-4 ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

16
[ 128293-62-9 ]
[ 535937-59-8 ]
[ 535937-76-9 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 1607 - 1610.

17
[ 128293-62-9 ]
[ 535937-85-0 ]
1-methyl-4-({1-methyl-4-[2-(4-trifluoromethyl-benzenesulfonyl)-ethoxycarbonylamino]-1H-imidazole-2-carbonyl}-amino)-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 1607 - 1610.

18
[ 128293-62-9 ]
[ 535937-82-7 ]
1-methyl-4-({1-methyl-4-[2-(4-trifluoromethyl-benzenesulfonyl) ethoxycarbonylamino]-1H-pyrrole-2-carbonyl}-amino)-1H-imidazole-2-carboxylic Acid Ethyl Ester [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 1607 - 1610.

19
[ 128293-62-9 ]
[ 150807-22-0 ]
[ 454646-16-3 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 4295 - 4300.

20
[ 28920-43-6 ]
[ 128293-62-9 ]
4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 2493 - 2503.

21
C₁₀H₈ClF₃O₄S [ No CAS ]
[ 128293-62-9 ]
1-methyl-4-[2-(4-trifluoromethyl-benzenesulfonyl)-ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 2493 - 2503.

22
[ 865307-73-9 ]
[ 128293-62-9 ]
[ 865307-74-0 ]

Yield	Reaction Conditions	Operation in experiment
63%		The compound 7 was dissolved in methanol (94.4 ml), mixed with 10 % Pd/C (1.18 g) and stirred for four hours under hydrogen atmosphere. 10% Pd/C was removed from the reaction system with cerite filtration, so that the solvent was distilled out under a reduced pressure. Dimethylformamide (10 ml) was added to the residue and distilled out again under a reduced pressure. The residue was dissolved in dimethylformamide (10 mL) again, and mixed with the compound 8 (5. 9 g, 23.6mmol) (Baird, E. E. ; Dervan, P. B. J. Org. Chem. 1996, 118, 6141-6146), EDC (9.05 g, 47.2 mmol) and dimethylaminopyridine (288 mg, 2. 36 mmol), and stirred for 12 hours at a room temperature. Re-precipitation treatment with chloroform and ethyl acetate gave the compound 9 as white powder (5.9 g, 63%). 1HNMR(DMSO-d6) delta 1.28-1.30 (3H, t, J = 7.1 Hz), 3.85(3H, s), 3.93(3H, s), 3.98(3H, s), 4.25-4.29 (2H, dd, J = 7.1 Hz), 7.03(1H, d, J = 0.7 Hz), 7.22(1H, d, J = 2.0 Hz), 7.38(1H, s), 7.38(1H, s), 7.66(1H, s), 10.35(1H, s), 10.74(1H, s) ; 13CNMR(DMSO-d6) delta 14.3, 35.3, 35.7, 36.5, 60.8, 106.4, 115.6, 119.8, 121.6, 122.2, 126.5, 127.2, 131.0, 138.0, 139.0, 156.3, 158.7, 158.9: Anal. Calcd. for C18H12N4O3·H2O: C, 53.22; H, 4.89; N, 22.57. Found: C, 50.88; H,4.88; N,23.13.

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 10311 - 10322.
[2]Patent: EP1719777,2006,A1 .Location in patent: Page/Page column 17; 19-20.

23
[ 66493-39-8 ]
[ 128293-62-9 ]
[ 292070-18-9 ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

24
[ 128293-62-9 ]
[ 128293-64-1 ]
[ 292070-63-4 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6339 - 6351.
[2]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3780 - 3783.

25
[ 128293-62-9 ]
[ 77716-11-1 ]
[ 195387-59-8 ]

26
[ 128293-62-9 ]
[ 111331-82-9 ]
4-(3-tert-butoxycarbonylamino-benzoylamino)-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

27
[ 128293-62-9 ]
[ 83673-98-7 ]
4-[(2-tert-butoxycarbonylamino-thiazole-4-carbonyl)-amino]-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

28
[ 128293-62-9 ]
[ 292068-69-0 ]
4-[(4-tert-butoxycarbonylamino-thiophene-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

29
[ 128293-62-9 ]
[ 292068-77-0 ]
4-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

30
[ 128293-62-9 ]
[ 138730-81-1 ]
4-[(5-tert-butoxycarbonylamino-1H-indole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394.

31
[ 13138-78-8 ]
[ 128293-62-9 ]
[ 142211-80-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8539 - 8549.

32
[ 128293-62-9 ]
[ 2258-42-6 ]
[ 128293-78-7 ]

References: [1]Synthetic Communications,2008,vol. 38,p. 33 - 44.

33
[ 128293-62-9 ]
[ 918304-04-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8539 - 8549.

34
[ 128293-62-9 ]
(CH₃O)(CH₃OCO)C₆H₂(NH₂)NHC₅H₅N₃O(C₆H₅N₂O₃) [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8539 - 8549.

35
[ 128293-62-9 ]
[ 918304-05-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8539 - 8549.

36
[ 128293-62-9 ]
C₂₀H₂₁N₇O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8539 - 8549.

37
[ 128293-62-9 ]
[ 918304-06-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8539 - 8549.

38
[ 128293-62-9 ]
[ 142211-81-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8539 - 8549.
[2]Journal of the American Chemical Society,1992,vol. 114,p. 5911 - 5919.

39
[ 128293-62-9 ]
sodium 1-methyl-4-{4-(1-methylimidazole-2-carboxamido)-1-methylpyrrole-2-carboxamido}imidazole-2-carboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 10311 - 10322.

40
[ 128293-62-9 ]
C₄₇H₆₂N₁₈O₉ [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 10311 - 10322.

41
[ 128293-62-9 ]
[ 454646-17-4 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 4295 - 4300.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 128293-62-9

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CAS No.: 128293-62-9

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[ 128293-62-9 ] Synthesis Path-Downstream 1~41

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