1,2-Dichloroethane → HCID 856742, compound

HRID 1666569Notes

Reaction equation

HRID 1666569 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:11]1([C:16]2[S:20][C:19]([NH2:21])=[N:18][N:17]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[CH:11]1([C:16]2[S:20][C:19]([NH:21][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])=[N:18][N:17]=2)[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 99352-Fluorobenzoic acidHCID 181649HOAtHCID 20636875-cyclopentyl-1,3,4-thiadiazol-2-amine2×

Product 1

HCID 856742HCID 856742, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml scintillation vial was added 2-fluorobenzoic acid (845 mg, 5.0 mmol) and commercially available 5-cyclopentyl-1,3,4-thiadiazol-2-amine (intermediate 49) (700 mg, 5.0 mmol). To this was added EDC (960 mg, 5 0 mmol) and HOAt (675 mg, 5.0 mmol) followed by 25 ml DCM. The reaction mixture was stirred with a Teflon covered magnetic stir-bar at room temperature for overnight. The product was collected by ethyl acetate and 5% HCl solution work up, and then to purified by column (CH3OH/DCM, 1-10% gradient system), yielding N-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-2-fluorobenzamide (0.61 g, 42%) as solid.

Workup

  1. customThe product was collected by ethyl acetate and 5% HCl solution work up
  2. customto purified by column (CH3OH/DCM, 1-10% gradient system)

Sources & evidence

ORD record
ord-c4853dce10934154ba08b7a4ccf920d7
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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