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Chemical Structure| 1244948-92-2 Chemical Structure| 1244948-92-2

Structure of 1244948-92-2

Chemical Structure| 1244948-92-2

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Product Details of [ 1244948-92-2 ]

CAS No. :1244948-92-2
Formula : C4H2BrNOS
M.W : 192.03
SMILES Code : O=CC1=C(Br)N=CS1
MDL No. :MFCD12025491
InChI Key :FLPSVRVLOVLWCQ-UHFFFAOYSA-N
Pubchem ID :45480408

Safety of [ 1244948-92-2 ]

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

Application In Synthesis of [ 1244948-92-2 ]

* 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 [ 1244948-92-2 ]

[ 1244948-92-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1244948-92-2 ]
  • C30H39NO4Si [ No CAS ]
  • 5-benzhydryloxy-8-triisopropylsilanyloxy-thiazolo[4,5-b]quinoline-6-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
For example, methyl 3-amino-2, 5-DIHYDROXYBENZOATE A26. 10 IS reacted sequentially with one molar equivalent of chlorotriisopropylsilane and imidazole in dichloromethane, and then with excess diphenyldiazomethane, to produce the differentially protected compound A26.11. The product is then reacted, as described above, with 4-bromothiazole- 5-carboxaldehyde A26.12 (WO 9317681) to give 5-benzhydryloxy-8- TRIISOPROPYLSILANYLOXY-THIAZOLO [4,5-b] quinoline-6-carboxylic acid methyl ester A26.13. This material is then coupled, as described above, with 3,5-dichloro-N-methylbenzylamine A26.14 to produce 5-BENZHYDRYLOXY-8-TRIISOPROPYLSILANYLOXY-THIAZOLO [4,5-b] quinoline-6- carboxylic acid 3, 5-DICHLORO-BENZYLAMIDE A26.15. Treatment of the latter compound with tetrabutylammonium fluoride in tetrahydrofuran then forms the phenol A26.16, which is reacted in DIMETHYLFBRMAMIDE solution with a dialkyl bromoethyl phosphonate A26.17 (Aldrich) and potassium carbonate, to afford after deprotection the phosphonate ether A26.18
  • 2
  • [ 1244948-92-2 ]
  • methyl 3-amino-2-diphenylmethoxybenzoate [ No CAS ]
  • 5-benzhydryloxy-9-methyl-thiazolo[4,5-b]quinoline-6-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
For example, methyl 3-amino-2-diphenylmethoxybenzoate A27. 12 IS reacted with 5- acetyl-4-bromothiazole A27.13 (WO 9317681) to afford after cyclization of the initial displacement product, 5-benzhydryloxy-9-methyl-thiazolo [4, 5-b] quinoline-6-carboxylic acid methyl ester A27.14. Reaction with N-BROMOSUCCINIMIDE in hexachloroethane then yields the bromomethyl analog A27.15, and this material is reacted with a trialkyl phosphite in an Arbuzov reaction to give the phosphonate A27.16. The product is then reacted with 3,5-dichlorobenzyl methylamine A27.17 and trimethyl aluminum to afford after deprotection the phosphonate A27.18.
  • 3
  • [ 1244948-92-2 ]
  • [ 57260-71-6 ]
  • [ 1449368-70-0 ]
YieldReaction ConditionsOperation in experiment
10 mg With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 - 50℃; for 49h; A solution of intermediate 114.1 (50mg), 1-Boc-piperazine (74mg) and DIPEA (0.067ml_) in THF (1.5ml) was stirred at RT for 1 h, then at 50C for 2days. The reaction mixture was diluted with water and extracted with DCM. The org. layers were dried (Na2SO4) and evaporated in vacuo. CC (silica gel, eluent Heptan/EA 7:3) afforded 10mg of yellow oil. LC- MS (B): tR = 0.80 min; [M+H]+: 298.17.
10 mg With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 - 50℃; for 49h; A solution of intermediate 114.1 (50 mg), 1-Boc-piperazine (74 mg) and DIPEA (0.067 mL) in THF (1.5 mL) was stirred at RT for 1 h, then at 50 C. for 2 days. The reaction mixture was diluted with water and extracted with DCM. The org. layers were dried (Na2SO4) and evaporated in vacuo. CC (silica gel, eluent Heptan/EA 7:3) afforded 10 mg of yellow oil. LC-MS (B): tR=0.80 min; [M+H]+: 298.17.
  • 4
  • [ 262444-15-5 ]
  • [ 1244948-92-2 ]
YieldReaction ConditionsOperation in experiment
708 mg With Dess-Martin periodane; In dichloromethane; at 20℃; for 18h;Inert atmosphere; To a pale yellow solution of (4-bromothiazol-5-yl)methanol (870mg) in DCM (25ml_) was added DMP (2.16g) at RT. The resulting yellow suspension was stirred at RT under argon for 18h. EA and aq. sat. NaHC03 were added to the reaction mixture and stirred for 5min. Water was added and the mixture was extracted with DCM three times. The combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. CC (Biotage, SNAP 50g cartridge, solvent A: Hept; solvent B: EA; gradient in %B: 10 for 5CV, 10 to 30 over 2CV, 30 for 3CV) afforded 708mg of yellow solid. 1H-NMR (CDCI3): 10.0 (s, 1 H); 9.04 (s, 1 H).
708 mg With Dess-Martin periodane; In dichloromethane; at 20℃; for 18h;Inert atmosphere; To a pale yellow solution of (4-bromothiazol-5-yl)methanol (870 mg) in DCM (25 mL) was added DMP (2.16 g) at RT. The resulting yellow suspension was stirred at RT under argon for 18 h. EA and aq. sat. NaHCO3 were added to the reaction mixture and stirred for 5 min. Water was added and the mixture was extracted with DCM three times. The combined org. layers were dried over MgSO4, filtrated off and evaporated in vacuo. CC (Biotage, SNAP 50 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 5CV, 10 to 30 over 2CV, 30 for 3CV) afforded 708 mg of yellow solid. 1H-NMR (CDCl3): 10.0 (s, 1H); 9.04 (s, 1H)
  • 5
  • [ 1244948-92-2 ]
  • [ 52476-87-6 ]
  • 2-chloro-4-(pyrazolo[3.4-d]thiazol-1-yl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
<strong>[1244948-92-2]4-bromothiazole-5-carboxaldehyde</strong> (0.96 g, 5 mmol) and 2-chloropyrimid-4-ylhydrazine (720 mg, 5 mmol) in ethanol (20 mL) containing acetic acid (10 mg, 0.17 mmol) is refluxed for 2h to form the hydrazone, and then the volatiles are removed rigorously under reduced pressure as described in Chinese J Chem 29, 1199 (2011). The residue is dissolved in DMSO (5 mL), and K3PO4 (2.12 g 10 mmol) and CuI (1 mg, 0.005 mmol) are added, and the reaction mixture is heated to 100 C under Ar for 12 hrs. The reaction mixture is cooled to 25 C, poured onto water (100 mL) and extracted with EtOAc (3 x 25 mL). The combined organic extracts are rinsed with water (2 x 25mL) saturated brine (25 mL) and dried (MgSO4). The solvent is removed under reduced pressure, and the residue purified by silica gel chromatography to give 2-chloro-4-(pyrazolo[3.4-d]thiazol-1-yl)pyrimidine.
 

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