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Chemical Structure| 89226-13-1 Chemical Structure| 89226-13-1

Structure of 89226-13-1

Chemical Structure| 89226-13-1

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Product Details of [ 89226-13-1 ]

CAS No. :89226-13-1
Formula : C7H14N2O2S
M.W : 190.26
SMILES Code : O=C(OC(C)(C)C)NCC(N)=S
MDL No. :MFCD09025922
InChI Key :AGBIUUFZUPNDTM-UHFFFAOYSA-N
Pubchem ID :5324304

Safety of [ 89226-13-1 ]

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

Application In Synthesis of [ 89226-13-1 ]

* 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.

  • Downstream synthetic route of [ 89226-13-1 ]

[ 89226-13-1 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 421-20-5 ]
  • [ 89226-13-1 ]
  • [ 140903-34-0 ]
  • 3
  • [ 35150-09-5 ]
  • [ 89226-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With Lawessons reagent; In tetrahydrofuran; at 20℃; for 16h; To compound 386 (21.63 g, 0.124 mol) dissolved in THF (400 mL) was added Lawesson reagent (30.13 g, 0.074 mol). Stirred at room temperature for 16 h then concentrated. Purified by silica gel chromatography (eluant: 3% MeOH- CH2CI2) then re-purified by silica gel chromatography (eluant: 2% MeOH- CH2Cl2) to give 23.59 g (100%) of the product 387 as a light green solid. MS m/e: 135 (M+2-tBu). For n=2: MS m/e: 149 (M+2-tBu)
78% With Lawessons reagent; In tetrahydrofuran; at 20℃; for 24h; Carbamoylmethyl-carbamic acid tert-butyl ester (10.88 grams, 62.46 mmol) and Lawesson's Reagent (15.66 grams, 38.72 mmol) were dissolved in THF (200 ml) and stirred under a nitrogen atmosphere at ambient temperature for 24 hours. The solvent was removed and the residue purified by column chromatography on silica (20% EtOAc/ hexanes) to yield Compound 14.2 (9.21 grams, 48.41 mmol, 78%). IH NMR (400 MHz, DMSO-d6) delta ppm 1.36 (s, 9 H) 3.80 (m, 2 H) 7.03 (m, 1 H) 8.99 (m, 1 H) 9.66 (m, 1 H).
60% With Lawessons reagent; In dichloromethane; at 20℃; for 16h;Inert atmosphere; Lawesson?s reagent (893 mg, 4.25 mmol) was added to a solution of glycineamide (740 mg, 4.25 mmol) in dry CH2Cl2 (50 mL) and the reaction mixture was stirred under N2 atmosphere at room temperature for 16 h. The reaction was quenched by addition of saturated aqueous NaHCO3 and was stirred for 1 h before been extracted with EtOAc (3 x 15 mL). The organic layers were washed with brine (20 mL); dried with MgSO4 and the solvent evaporated under reduced pressure to give the crude product wich was purified by flash chromatography (hexane/ EtOAc, 1:1) to give 8 (466 mg, 60 %) as a white solid. Rf = 0.51 (hexane/ EtOAc, 1:1); 1H NMR (400MHz, CDCl3) delta 1.46 (s, 9H), 4.16 (d, 2H, J = 6.1 Hz), 5.33 (bs, 1H), 7.66 (bs, 1H), 7.89 (bs, 1H). 13C NMR (100MHz, CDCl3) delta 28.3 (3C), 51.4, 81.1, 156.4, 205.1.
51% With Lawessons reagent; In tetrahydrofuran; at 20℃;Inert atmosphere; To a solution of N-Boc-glycinamide (2.5 g, 14.3 mmol, 1 equiv.) in anhydrous THF (20 mL) was added Lawesson's reagent (3.5 g, 8.6 mmol, 1 equiv.) under argon. The reaction mixture was stirred at rt overnight. The solvent was evaporated and the residue purified by flash chromatography using EtOAc/CH2Cl2 (1/9) to give 5 as a white solid (1.4 g, 51%)
42% With Lawessons reagent; In dichloromethane; at 20℃; for 12h; To a solution of Boc-Gly-NH2 (11 g, 62.9 mmol) in CH2Cl2 (300 mL) was added Lawesson's Reagent (13.2 g, 32.7 mmol). After stirring at rt for 12 h, the mixture was concentrated. Purification of the residue (SiO2; 50% Et2O in hexanes) provided the desired product (5.0 g, 42%).
44 g With Lawessons reagent; In tetrahydrofuran; at 20℃; for 5h; Compound 23 (42.59g, 244 . 5mmol) dissolved in tetrahydrofuran (500 ml), cooled to 0 C, plus olausson reagent (59.34g, 146 . 7mmol), stirring at room temperature to 5h, decompression turns on lathe thf, the residue is poured into the ice and saturated sodium bicarbonate solution, ethyl acetate extraction of the organic phase (500mLx3), combined with the phase, the organic phase with saturated salt water washing, dry anhydrous sodium sulfate, concentrated, the residue is dissolved in silica gel column chromatography to obtain white solid compound 24 (44g, 95%). 1 HNMR (400MHz, CDCl 3): delta 7.82 (br, 1H), 7.52 (br, 1H), 5.25 (br, 1H), 4.16 (d, J= 6.0Hz, 2H), 1.46 (s, 9H).

  • 4
  • [ 90929-73-0 ]
  • [ 89226-13-1 ]
  • [ 1001412-80-1 ]
YieldReaction ConditionsOperation in experiment
81% In acetonitrile; at 20 - 80℃; for 22h; Compound 14.1 (0.308 grams, 1.28 mmol) was mixed with Compound 14.2 (0.245 grams, 1.28 ramol) and AcCN (6 ml) was added. The reaction was stirred at ambient temperature for 20 hours followed by 80 C for 2 hours. The mixture was cooled to room temperature, diluted with EtOAc, washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and concentrated to yield Compound 14.3 (0.344 grams, 1.04 mmol, 81 %). ES (+) MS m/e = 331 (M+l).
  • 5
  • [ 1001412-89-0 ]
  • [ 89226-13-1 ]
  • [ 1001412-91-4 ]
YieldReaction ConditionsOperation in experiment
19% In ethanol; for 16h;Heating / reflux; Compound 17.1 (1.0 gram, 3.95 mmol) and Compound 14.2 (0.752 grams, 3.95 mmol) were dissolved in EtOH (20 ml) and heated at reflux for 16 hours. The mixture was cooled to ambient temperature, diluted with DCM, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated to yield Compound 17.2 (0.254 grams, 0.737 mmol, 19%). ES (+) MS m/e = 345 (M+l).
  • 8
  • [ 4530-20-5 ]
  • Fmoc-L-Leu-F [ No CAS ]
  • [ 89226-13-1 ]
  • 12
  • [ 89226-13-1 ]
  • {N-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-carbamimidoylmethyl}-carbamic acid tert-butyl ester; hydrobromide [ No CAS ]
  • 13
  • [ 4530-20-5 ]
  • [ 89226-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With Lawessons reagent; In dichloromethane; at 25℃; for 16h; Boc-glycine (2.34 g, 0.134 mmol) was dissolved in dichloromethane (130 mL) and treated with Lawesson's reagent (2.9 g, 0.52 equivalents) and the mixture was stirred at 25 C. for 16 h. The mixture was filtered and the solvents were evaporated. The residue was purified using dichloromethane:ethyl acetate (1:1) to give 2.56 g (100%) of the thioamide.
  • 22
  • [ 89226-13-1 ]
  • [ 182120-92-9 ]
  • 26
  • [ 89226-13-1 ]
  • 2-[2-(tert-Butoxycarbonylamino-methyl)-thiazol-4-yl]-4,5-dihydro-oxazole-4-carboxylic acid methyl ester [ No CAS ]
  • 27
  • [ 89226-13-1 ]
  • [ 159379-66-5 ]
  • 28
  • [ 89226-13-1 ]
  • 2-[2-((S)-1-[2-(tert-Butoxycarbonylamino-methyl)-thiazole-4-carbonyl]-amino}-ethyl)-thiazole-4-carbonyl]-amino}-acrylic acid methyl ester [ No CAS ]
  • 29
  • [ 89226-13-1 ]
  • [ 88621-29-8 ]
  • 33
  • [ 89226-13-1 ]
  • [ 609-15-4 ]
  • ethyl 2-(tert-butoxycarbonylamino-methyl)-4-methyl-thiazole-5-carboxylate [ No CAS ]
  • 34
  • [ 4755-81-1 ]
  • [ 89226-13-1 ]
  • [ 232280-99-8 ]
YieldReaction ConditionsOperation in experiment
57.8% In methanol; at 20 - 60℃; for 50h; N-BOC-Glycine [sic] thioamide (10.0 g, 52.6 mmol) was introduced into methanol (70 ml), and methyl 2-chloroacetoacetate (7.9 g, 52.6 mmol) was added. The mixture was warmed for 2 hours at 60 C. and subsequently stirred for 48 hours at room temperature. The methanol was removed on a rotary evaporator and the residue was extracted by stirring with acetone/diethyl ether. The precipitate which remained was filtered off with suction and the filtrate was concentrated. The solid obtained from the filtrate constituted the product (pure after TLC and HPLC). Yield: 8.7 g (30.4 mmol, 57.8%). ESI-MS: 287 (M+H+)
  • 35
  • [ 363-58-6 ]
  • [ 89226-13-1 ]
  • [ 232281-06-0 ]
YieldReaction ConditionsOperation in experiment
24.5% N-BOC-Glycine [sic] thioamide (5.0 g, 26.28 mmol) was dissolved in acetonitrile (60 ml), and a solution of ethyl 2-chloro-4,4,4-trifluoroacetoacetate (6.38 g, 26.28 mmol) was added dropwise at 5-10 C. Then, the mixture was stirred for a further 30 minutes at 5 C. and for 12 hours at room temperature. The batch was then cooled to 0 C., and triethylamine (12 ml, 86.77 mmol) was added dropwise. After the mixture had been stirred for 20 minutes at 0 C., the yellow suspension had changed into a clear reddish-brown solution. Then, thionyl chloride (2.1 ml, 28.89 mmol) was slowly added dropwise at 0 C. After the mixture had been stirred for 20 minutes at 0 C., it was warmed to room temperature for a further hour. The solvent was removed on a rotary evaporator, and the residue was taken up in water (100 ml) and extracted repeatedly with ethyl acetate. The combined organic phases were dried (Na2AO4) and concentrated. The crude product was purified by chromatography (silica gel MeOH:DCM=2:98). Yield: 2.2 g (6.4 mmol, 24.5%)
  • 36
  • [ 36437-19-1 ]
  • [ 89226-13-1 ]
  • 2-(N-t-butoxycarbonylamino)methyl-5-formylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium bromide; calcium carbonate; In ethyl acetate; N,N-dimethyl-formamide; a 2-(N-t-butoxycarbonylamino)methyl-5-formylthiazole To 33 ml of a DMF solution containing 5.5 g (purity 65%) of chloromalondialdehyde, 4.7 g of calcium carbonate, 4.8 g of sodium bromide and 5.8 g of (N-t-butoxycarbonyl)aminoacetothioamide were added, and the mixture was then stirred at 60 C. for 11 hours. Then, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in 300 ml of ethyl acetate. The solution was washed twice with an aqueous saturated sodium bicarbonate solution and once with a 10% saline solution, dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 4.57 mg of 2-(N-t-butoxycarbonylamino)methyl-5-formylthiazole. NMR (CDCl3) delta: 1.48 (9H, s), 4.66 (2H, d, J=6.2 Hz), 5.33 (1H, br.s), 8.32 (1H, s), 10.00 (1H, s)
  • 37
  • ethyl 3-bromo-2-oxosuccininate [ No CAS ]
  • [ 89226-13-1 ]
  • ethyl 2-(((tert-butoxycarbonyl)amino)methyl)-5-methylthiazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With calcium carbonate; In N,N-dimethyl-formamide; a 2-(N-t-butoxycarbonylamino)methyl-4-ethoxycarbonyl-5-methylthiazole To 250 ml of an anhydrous DMF solution containing 24.6 g of ethyl 3-bromo-2-oxosuccininate, 21.5 g of (N-t-butoxycarbonylamino)acetothioamide and 6.9 g of calcium carbonate were added, and the mixture was then stirred at 40 C. for 15 hours. After diluted with ethyl acetate, the reaction solution was filtered through Celite, followed by washing with water, an aqueous saturated sodium hydrogencarbonate solution and a saturated saline solution in succession. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 23.5 g of 2-(N-t-butoxycarbonylamino)methyl-4-ethoxycarbonyl-5-methylthiazole as a yellow crystal. NMR (CDCl3) delta: 1.41 (3H, t, J=7.1 Hz), 2.75 (3H, s), 4.41 (2H, q, J=7.1 Hz), 4.55 (2H, d, J=6.0 Hz),, 5.26-5.36 (1H, br.s) MS (EI): 300 (M+)
  • 38
  • [ 117334-68-6 ]
  • [ 89226-13-1 ]
  • [ 117333-91-2 ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane; acetone; Preparation 41 To a solution of (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (20 g) in a mixture of methanol (200 ml) and dichloromethane (200 ml) was added <strong>[89226-13-1]2-(N-t-butoxycarbonylamino)thioacetamide</strong> (20 g) at room temperature. After stirring at ambient temperature for 12 hours, the mixture was poured into ethyl acetate, washed with saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated, and the obtained oil was subjected to a column chromatography on silica gel and eluted with a mixture of acetone and dichloromethane (1:5, V/V) to give (2S,4R)-2-[2-(N-t-butoxycarbonylamino)methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (9.7 g). IR (CH2 Cl2): 1705, 1605 cm-1. NMR (CDCl3, delta): 1.42 (9H, s), 2.4-2.7 (2H, m), 3.02 (3H, s), 3.6-4.2 (2H, m), 4.52 (2H, d, J=7 Hz), 5.0-5.6 (3H, m), 6.9-7.8 (3H, m), 8.0-8.3 (2H, m).
  • 39
  • [ 70-23-5 ]
  • [ 89226-13-1 ]
  • [ 182120-82-7 ]
  • 40
  • [ 5469-26-1 ]
  • [ 89226-13-1 ]
  • [ 1048675-21-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 20℃; for 12h; To a solution of the above compound (0.2 g, 1.05 mmol) in EtOH (5 mL) was added 1-bromo-3,3-dimethyl-butan-2-one (0.188 g, 1.05 mmol). After stirring 12 h at rt, the mixture was concentrated. Purification of the residue (SiO2; 20% EtOAc in hexanes) provided the desired product. HPLC: Rt=1.79. MS (ESI): mass calcd. for C13H22N2O2S, 270.1; m/z found, 271.1 [M+H]+.
  • 41
  • [ 89226-13-1 ]
  • [ 822-87-7 ]
  • [ 651706-15-9 ]
YieldReaction ConditionsOperation in experiment
A solution of 2-chlorocyclohexanone (58 muL, 0.5 mmol), tert-butyl-2-amino-2-thioxoethylcarbamate (105.7 mg, 0.5 mmol) in ethanol (2 mL) was stirred at room temperature for 1.5 hours, then at 80C for 40 hours. The reaction was then concentrated. Ethyl acetate and a diluted hydrochloric acid solution were added to the crude product. The solution was extracted with diethyl ether and ethyl acetate. These organic layers were discarded. The aqueous layer was basified with aqueous sodium hydroxide to pH = 10, and then extracted with diethyl ether and ethyl acetate. Combined organic extracts were dried over sodium sulfate, filtered and evaporated to give crude 1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)methanamine (30.9 mg, 36%) as a brown oil which was used in the next steps without purification. ESI-MS m/z 169 (M+H)+.
  • 42
  • [ 89226-13-1 ]
  • [ 534-07-6 ]
  • [ 74-89-5 ]
  • [ 1260716-34-4 ]
YieldReaction ConditionsOperation in experiment
Example 471A (0.5 g) was dissolved in isopropanol (10 mL) and treated with dichloroacetone (0.33 g, 1 equivalent) and the mixture was stirred at 25 C. for 16 h. The solvents were evaporated, and the crude residue was dissolved in isopropanol (2 mL) and treated with 40% methylamine in water (5 mL, 25 equivalents). The solvents were evaporated, and the residue was partitioned between ethyl acetate and sat NaHCO3. The organic layer was separated, dried over MgSO4, filtered, and the solvents were evaporated to give 0.48 g of the title compound.
Example 471Btert-butyl{4-[(methylamino)methyl]-1,3-thiazol-2-yl}methylcarbamateExample 471A (0.5 g) was dissolved in isopropanol (10 mL) and treated with dichloroacetone (0.33 g, 1 equivalent) and the mixture was stirred at 25 C. for 16 h. The solvents were evaporated, and the crude residue was dissolved in isopropanol (2 mL) and treated with 40% methylamine in water (5 mL, 25 equivalents). The solvents were evaporated, and the residue was partitioned between ethyl acetate and sat NaHCO3. The organic layer was separated, dried over MgSO4, filtered, and the solvents were evaporated to give 0.48 g of the title compound.
 

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