1,2-Dichloroethane → HCID 24959464, compound

HRID 1666568Notes

Reaction equation

HRID 1666568 reaction equation
C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[S:26][C:25]([NH2:27])=[N:24][N:23]=2)=[CH:18][CH:17]=1.[CH2:28]([NH:30][S:31]([C:34]1[CH:35]=[C:36]([F:44])[C:37]([F:43])=[C:38]([CH:42]=1)[C:39](O)=[O:40])(=[O:33])=[O:32])[CH3:29].CN(C=O)C>>[CH2:28]([NH:30][S:31]([C:34]1[CH:35]=[C:36]([F:44])[C:37]([F:43])=[C:38]([CH:42]=1)[C:39]([NH:27][C:25]1[S:26][C:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)=[N:23][N:24]=1)=[O:40])(=[O:33])=[O:32])[CH3:29]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 181649HOAtHCID 5542085-(4-Fluorophenyl)-1,3,4-thiadiazol-2-amineHCID 59591413HCID 59591413, compound

Product 1

HCID 24959464HCID 24959464, compoundYield 19%

Procedure

To a 20 ml scintillation vial was added EDC (54 mg, 0.283 mmol), HOAt (38 mg, 0.283 mmol) and commercially available 5-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine (55 mg, 0.283 mmol). To this was added 5-[(ethylamino)sulfonyl]-2,3-difluorobenzoic acid as a solution in 2 ml DMF (75 mg, 0.283 mmol based on theoretical yield of preceding). The reaction mixture was stirred at room temperature overnight with a Teflon covered magnetic stir-bar. The reaction mixture was then concentrated to ˜1 ml and the residue was purified using a Gilson preparative HPLC system with a Waters Xterra (C-18) column 100 mm by 50 mm ID, eluting with 30% B to 60% B in 10 min, where A=H2O and B=CH3CN pumped at 150 mL/min to yield 5-[(Ethylamino)sulfonyl]-2,3-difluoro-N-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamide as a white solid (12 mg, 19%).

Workup

  1. concentrationThe reaction mixture was then concentrated to ˜1 ml
  2. customthe residue was purified
  3. washeluting with 30% B to 60% B in 10 min

Sources & evidence

ORD record
ord-c6cbdb51e3f448508a96e425c9357db1
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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