1,2-Dichloroethane → HCID 59591388, compound

HRID 1666563Notes

Reaction equation

HRID 1666563 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH2:15][C:16](F)(F)F)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.F[C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:30]2[S:34][C:33]([NH2:35])=[N:32][N:31]=2)([CH3:29])[CH3:28])=[CH:23][CH:22]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>>[CH2:15]([NH:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([NH:35][C:33]1[S:34][C:30]([C:27]([CH3:29])([C:24]2[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=2)[CH3:28])=[N:31][N:32]=1)=[O:6])(=[O:13])=[O:12])[CH3:16]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 297870262-Fluoro-5-[[(2,2,2-trifluoroethyl)amino]sulfonyl]benzoic acid2×HCID 59591400HCID 59591400, compound

Product 1

HCID 59591388HCID 59591388, compoundYield 5.8%

Procedure

To 2-fluoro-5-{[(2,2,2-trifluoroethyl)amino]sulfonyl}benzoic acid (intermediate 25)(30.1 mg 0.1 mmol) and above 5-[1-(4-fluorophenyl)-1-methylethyl]-1,3,4-thiadiazol-2-amine (23.7 mg, 0.1 mmol) in 2.0 mL of mixed solvent (DCM:DMF=10:1) were 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 20% B to 99% 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 (2.6 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified
  3. washeluting with 20% B to 99% B in 10 min

Sources & evidence

ORD record
ord-cceb10601014468abd6b2fd7d76b2c7d
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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