1,2-Dichloroethane → HCID 24960194, compound

HRID 1666575Notes

Reaction equation

HRID 1666575 reaction equation
[Cl:1][C:2]1[C:3]([F:17])=[C:4]([CH:8]=[C:9]([S:11]([NH:14][CH2:15][CH3:16])(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:32][C:33]([C:41]1[S:45][C:44]([NH2:46])=[N:43][N:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:34]>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([F:17])=[C:4]([CH:8]=[C:9]([S:11]([NH:14][CH2:15][CH3:16])(=[O:13])=[O:12])[CH:10]=1)[C:5]([NH:46][C:44]1[S:45][C:41]([C:33]([CH3:34])([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:32])=[N:42][N:43]=1)=[O:7]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 234059031032463-93-6HCID 59591390HCID 59591390, compound

Product 1

HCID 24960194HCID 24960194, compoundYield 109.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-chloro-5-[(ethylamino)sulfonyl]-2-fluorobenzoic acid (60 mg, 0.213 mmol) in DMF (3 ml) and DCM (3 ml) was added EDC (40.8 mg, 0.213 mmol) and HOBt (32.6 mg, 0.213 mmol). After 10 mins, 5-(1-methyl-1-phenylethyl)-1,3,4-thiadiazol-2-amine (41.6 mg) was added. The reaction mixture was stirred at rt overnight, concentrated and purifed by HPLC to give the title compound (100 mg) LC/MS: m/z 482.8 (M+H), rt 2.05 min.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-08ece714261e45b78f2d616535fec2ad
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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