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Chemical Structure| 138588-22-4 Chemical Structure| 138588-22-4

Structure of 138588-22-4

Chemical Structure| 138588-22-4

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Product Details of [ 138588-22-4 ]

CAS No. :138588-22-4
Formula : C7H6N4S
M.W : 178.21
SMILES Code : NC1=NC(C2=NC=CC=C2)=NS1
MDL No. :MFCD11845692
InChI Key :UIJGGAZDQUJDGK-UHFFFAOYSA-N
Pubchem ID :21688995

Safety of [ 138588-22-4 ]

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

Application In Synthesis of [ 138588-22-4 ]

* 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 [ 138588-22-4 ]

[ 138588-22-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 887623-91-8 ]
  • [ 138588-22-4 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In ethanol; at 70.0℃; A solution of 2-(5-chloro-l,2,4-thiadiazol-3-yl)pyridine in 2 M ammonia in EtOH (10 ml) was heated overnight at 70C. Volatiles were removed by concentration under reduced pressure. Purification by chromatography on silica (eluted with 0 -> 10% MeOH/CH2Cl2 + 0 -> 1 % NH4OH) gave 3-(pyridin-2-yl)-l ,2,4-thiadiazol-5-amine.
  • 2
  • [ 138588-22-4 ]
  • [ 74-11-3 ]
  • 4-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃;Inert atmosphere; 3-Pyridm-2-yl-[l,2,4]thiadiazol-5-yIamine (50 mg, 0.28 mmol) and p-chlorobenzoic acid (44 mg, 0.28 mmol) were mixed in 1 mL of anhydrous dimethvlformamide, to which solution was added N,N-diisopropylethylamine (0.1 mL, 0.58 mmol) followed by addition of 1 - [his(dimethylammo)methylene]~ 1H- 1 ,2,3-triazolo[4,5-b]pyridinium 3 -oxide hexafluorophosphate (1 14 mg, 0.30 mmol). The mixture was stirred under nitrogen at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to obtain Compound 7 as a white solid (53.5 mg, 60%). NMR (400 MHz, DMSO-rfe) delta ppm 7.36 - 7.64 (m, 1 H) 7.69 (d, J=8.69 Hz, 2 H) 7.91 - 8.10 (m, 1 H) 8.12 - 8.34 (m, 3 H) 8.72 (d, J=4.00 Hz, 1 H); LCMS (M/Z): M+HT' 317.
  • 3
  • [ 138588-22-4 ]
  • [ 98-60-2 ]
  • 4-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 20.0℃; for 16.0h; 3-(Pyridin-2-yl)- 1 ,2,4-thiadiazol-5-amine (50 rag, 0.28 mmoi) was dissolved in 1.5 ml, pyridine. 4-Chlorobenzenesulfonyl chloride (65 mg, 0.31 mmol) was then added. The mixture was stirred for 16 hours at room temperature. The reaction was partitioned between dichloroniethane and water. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to obtain Compound 14 as a tan solid. LCMS (M/Z): 352 (M + H). NMR (400 MHz, acetone) delta ppm 7.53 - 7.63 (m, 3 H) 7.91 (d, J 8.64 Hz, 2 H) 8.03 (td, J=7.75, 1.54 Hz, 1 H) 8.24 (d, J 8.00 Hz, 1 IT) 8.66 (d, J 4.49 Hz, 1 H).
  • 4
  • [ 32990-47-9 ]
  • [ 138588-22-4 ]
  • 4-methyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]thiophene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydroxide; In 1,4-dioxane; at 50.0℃; for 16.0h; 3-Pyridin-2-yl-[l,2,4]thiadiazol-5-ylatnine (50 mg, 0.28 mmol) was placed in a vial and dissolved in dioxane (1.5 mL) and then added 3 N NaOH (1.5 mL), Then 4- methyithiophene-2-carboxiyl chloride (45 mg, 0.28 mmol) was added and the reaction heated to 50 C for 16 h. The reaction was then diluted with water and acidified with AcOH to force precipitation. The precipitates were collected by filtration. The collected solid was redissolved and concentrated onto celite (5 g). Then purified by normal phase chromatography (solvent A CH2C12, solvent B CH2Cl2/MeOH/ H40H 90: 10: 1, gradient from 0 - 60% B). Collected the desired product (72 mg, 0.24 mmol, 86%). NMR (400 MHz, DMSO-rf6) delta pm 2.25 (s, 3 H) 7.49 (ddd, J=7.55, 4.75, 1.12 Hz, 1 H) 7.65 (s, 1 H) 7.95 (id, J-7.74, 1.81 Hz, 1 H) 8.13 (d, ,/ 1.02 Hz, 1 H) 8.20 (d, J-7.91 Hz, 1 H) 8.62 - 8.74 (m, 1 H) 13.75 (br. s., i H); LCMS (M/Z): M i i 303.
  • 5
  • [ 138588-22-4 ]
  • [ 2215-77-2 ]
  • 4-phenoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50.0℃; for 16.0h;Inert atmosphere; 3-Pyridin-2-y]-[l ,2,4]thiadiazol-5-ylamine (50 mg, 0.28 mmol), 4~phenoxybenzoic acid (120 mg, 0.56 mmol), and l -[is(dimethyiamino)methylene]-lH-l,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (128 mg, 0.34 mmol) was placed in a vial. Then dissolved in DMF (3 mL, anhydrous), added N,N-diisopropylet ylamine (98 ,uL, 0.56 mmol), and stirred at 50 C for 16 h. The reaction was diluted with water and extracted with EtOAc (x 3). The combined organic layers were dried and concentrated onto celite. Purified by normal phase chromatography (solvent A CC12, solvent B CH2Cl2/MeOH. NH4OH 90: 10: 1, gradient from 0 - 50% B). Collected the desired product (25.2 mg, 0.0674 mmol, 24%). JH NMR (400 MHz, DMSO-t e) 6 ppm 7.1 1 (d, J-8.83 Hz, 2 H) 7.16 (d, J-7.66 Hz, 2 H) 7.23 - 7.31 (m, 1 H) 7.43 - 7.56 (m, 3 H) 7.98 (td, J=7.75, 1.73 Hz, i H) 8.24 (d, J-8.74 Hz, 3 H) 8.72 (d, J=4.34 Hz, 1 H) 13.71 (br. s., 1 H); LCMS (M/Z): M-H-f 375.
  • 6
  • [ 138588-22-4 ]
  • [ 5416-93-3 ]
  • 1-(4-methoxyphenyl)-3-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% In tetrahydrofuran; at 50.0℃; 3-Pyridin-2-yl-[l,2,4]thiadiazo{-5-ylamine (50 mg, 0.28 mmol) was dissolved in 1 mL of anhydrous tetrahydrofuran, to which solution was added p-methoxyphenyl isocyanate (36 muEpsilon, 0.28 mmol). The mixture was stirred at 50 C overnight. Precipitation formed which was filtered and rinsed with methanol to yield a white solid (47,9 mg, 52%). NMR (400 MHz, DMSO-ifc) delta ppm 3.74 (s, 3 H) 6.81 - 7.06 (m, 2 H) 7.32 - 7.46 (m, 2 H) 7.46 - 7.57 (m, 1 H) 7.83 FontWeight="Bold" FontSize="10" 8.06 (m, 1 i n 8.19 i d. ./ 7.S6 Hz, 1 H) 8.60 · 8.90 (m, 1 H) 9.12 (s, 1 I I ) 1 1.49 (s, 1 H); LCMS (M/Z): M+H " 328.
 

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