1,2-Dichloroethane → HCID 59591388, compound

HRID 1666561Notes

Reaction equation

HRID 1666561 reaction equation
[CH2:1]([NH:3][S:4]([C:7]1[CH:8]=[CH:9][C:10]([F:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=O)(=[O:6])=[O:5])[CH3:2].[CH3:17][C:18]([C:26]1[S:30][C:29]([NH2:31])=[N:28][N:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>>[CH2:1]([NH:3][S:4]([C:7]1[CH:8]=[CH:9][C:10]([F:16])=[C:11]([CH:15]=1)[C:12]([NH:31][C:29]1[S:30][C:26]([C:18]([CH3:19])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:17])=[N:27][N:28]=1)=[O:14])(=[O:5])=[O:6])[CH3:2]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 12520985-[(ethylamino)sulfonyl]-2-fluorobenzoic acidHCID 234059031032463-93-6

Product 1

HCID 59591388HCID 59591388, compoundYield 15.6%

Procedure

To the mixture of 5-[(ethylamino)sulfonyl]-2-fluorobenzoic acid (24.7 mg, 0.1 mmol), prepared according to Scheme 4, and above crude 5-(1-methyl-1-phenylethyl)-1,3,4-thiadiazol-2-amine (21.9 mg, 0.1 mmol) in 2.0 mL of mixed solvents (DCM:DMF=10:1) was added EDC (19.2 mg, 0.1 mmol) and HOAt (13.6 mg, 0.1 mmol). The resultant mixture was stirred at room temperature for overnight, and then concentrated in vacuo. The residue was purified by using a Gilson preparative HPLC system with a Waters Xterra (C-18) column 100 mm by 50 mm ID, eluting with 10% B to 90% B in 10 min, where A=H2O and B=CH3CN pumped at 150 mL/min to yield 5-[(ethylamino)sulfonyl]-2-fluoro-N-[5-(1-methyl-1-phenylethyl)-1,3,4-thiadiazol-2-yl]benzamide (7.0 mg).

Workup

  1. customprepared
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified
  4. washeluting with 10% B to 90% B in 10 min

Sources & evidence

ORD record
ord-f5f6c338641d4b7db21085e150e17ddf
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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