5-Chloro-3-(1H-imidazol-1-yl)-1,2,4-thiadiazole → HCID 58654443, compound

HRID 1170529Notes

Reaction equation

HRID 1170529 reaction equation
[NH2:1][CH:2]([CH:17]([CH3:19])[CH3:18])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=1)=[O:4].Cl[C:21]1[S:25][N:24]=[C:23]([N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)[N:22]=1>CS(C)=O.C(N(CC)CC)C.[Cl-].[Na+].O>[O:12]1[C:11]2[CH:15]=[CH:16][C:8]([CH2:7][CH2:6][NH:5][C:3](=[O:4])[C@H:2]([NH:1][C:21]3[S:25][N:24]=[C:23]([N:26]4[CH:30]=[CH:29][N:28]=[CH:27]4)[N:22]=3)[CH:17]([CH3:19])[CH3:18])=[CH:9][C:10]=2[O:14][CH2:13]1

Participants

6

Reactant 2

HCID 452743615-Chloro-3-(1H-imidazol-1-yl)-1,2,4-thiadiazoleHCID 68690999HCID 68690999, compound

Product 1

HCID 58654443HCID 58654443, compoundYield 9.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Amino-N-(2-benzo[1,3]dioxol-5-yl-ethyl)-3-methyl-butyramide (135 mg, 0.51 mmol) was dissolved in DMSO (2 mL) and triethylamine (150 μL). Next, the 5-chloro-3-imidazol-1-yl-[1,2,4]thiadiazole (95.1 mg, 0.51 mmol) was added to the reaction vessel and it was stirred at room temperature for 16 hours. After this period, a portion of brine (50 mL) was added and the mixture was transferred to a separatory funnel and extracted with ethyl acetate (75 mL). The organic layer was dried over Na2SO4 and concentrated under vacuum. The crude material was purified by Flash Chromatography (0-50% ACN/DCM gradient) to afford 20.4 mg of pure product, N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-ylamino)-3-methyl-butyramide. [M+H]+ 414.84; 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.71 (s, 1H), 6.99 (s, 1H), 6.62-6.52 (m, 3H), 5.82-5.80 (m, 2H), 4.0 (Br s, 1H), 3.64-3.47 (m, 3H), 2.76-2.72 (m, 2H), 2.30-2.29 (m, 1H), 1.03-1.01 (m, 6H).

Workup

  1. waitAfter this period
  2. customthe mixture was transferred to a separatory funnel
  3. extractionextracted with ethyl acetate (75 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by Flash Chromatography (0-50% ACN/DCM gradient)

Sources & evidence

ORD record
ord-a144b203bcff4a659f2f71632e42d90b
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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