Structure of 143982-40-5
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CAS No. : | 143982-40-5 |
Formula : | C7H5N3O |
M.W : | 147.13 |
SMILES Code : | O=CC1=CN2C=CC=NC2=N1 |
MDL No. : | MFCD09994887 |
InChI Key : | BJPFFMZIQGNKKA-UHFFFAOYSA-N |
Pubchem ID : | 15152331 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; for 1.0h;Reflux; | General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With calcium carbonate; In water; for 1.0h;Reflux; | A mixture of compound 2 (1g, 4.95 mmol), CaCO3 (5g, 24.75 mmol) in water (30 mL) was refluxed for 1h. The reaction mixture was cooled to room temperature and extracted with ethylacetate and evaporated under reduced pressure to obtain the crude compound 3, which was purified by columnchromatography (silica gel: 60 - 120 mesh, eluent: 1% MeOH / CHCl3) to afford compound 3. Pale yellow solid, Yield: 60%; M.p: 209 - 210oC. IR (KBr): νmax 2934 (C-H aromatic), 1644 (C=O), 1543 (C=N),1213(C-N) cm-1; 1H NMR (400 MHz, CDCl3): d 9.96 (s, 1H), 9.66 (q, J = 6.8 Hz, 1H), 8.88 (q, J = 4.0 Hz,1 H), 8.70 (s, 1H), 7.43 (q, J = 6.4 Hz, 1 H). ESI-MS:m/z (rel.abund.%) 148.2 (M+H). [Found: C, 56.58; H,2.83.21; N, 27.98 C7H5N3O requires C, 57.14; H, 3.43;N, 28.56]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium carbonate; In ethanol; water; at 25.0℃; for 3.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium carbonate; In water; at 25.0℃; for 2.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.2-Amino-7-hydrox y-4- ( imidazo[1,2- a ]pyr imi -din-2-yl)-4H-chromene-3-carbonitrile (4a, C16H11N5O2)Usingresorcinol in water with 2 h reaction time. The pure product4a was obtained by crystallization with toluene/ethyl alcohol.Cream-colored solid; yield: 0.17 g (83%); m.p.: > 300 C(dec.); 1H NMR (600 MHz, DMSO-d6): δ = 9.86 (1H, s), 8.52(1H, dd, J = 3.90, 1.89 Hz), 8.48 (1H, dd, J = 6.88, 1.61 Hz),7.63 (1H, s), 7.11 (2H, s), 7.04 (1H, dd, J = 4.1, 2.73 Hz),6.73 (1H, t, J = 4.55 Hz), 6.46 (2H, m), 5.41 (1H, s) ppm;13C NMR (150 MHz, DMSO-d6): δ = 161.41, 158.20, 150.00,149.81, 148.58, 134.00, 132.59, 129.27, 125.14, 120.40,113.17, 109.90, 109.23, 103.04, 52.30, 30.56 ppm; IR (ATR): v = 3477, 3384, 3337, 3187, 3094, 2990, 2919, 2185, 1651,1617, 1592, 1497, 1398, 1318, 1279, 1139, 1111, 1037, 911,874, 839, 788, 773, 699, 667 cm-1; MS: m/z (%) = 306 (M+,100), 279 (40), 206 (36), 180 (36). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium carbonate; In ethanol; water; at 25.0℃; for 5.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium carbonate; In water; at 25.0℃; for 2.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium carbonate; In ethanol; water; at 25.0℃; for 2.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium carbonate; In water; at 25.0℃; for 2.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium carbonate; In ethanol; water; at 25.0℃; for 7.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition. |
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