1,2-Dichloroethane → HCID 67444739, compound

HRID 1666576Notes

Reaction equation

HRID 1666576 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.[CH2:18](Cl)CCl.C1C=C[C:25]2N(O)[N:29]=[N:28][C:26]=2[CH:27]=1.CC([C:36]1[S:40][C:39](N)=[N:38]N=1)(C)C>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:38][CH:39]1[N:28]([C:26]([CH3:25])([CH3:27])[CH3:18])[N:29]=[CH:36][S:40]1)=[O:7]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 170170ButhidazolamineHCID 59591390HCID 59591390, compound

Product 1

HCID 67444739HCID 67444739, compoundYield 15.5%

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-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-amine (46.7 mg) was added. The reaction mixture was stirred at rt overnight, concentrated and purifed by HPLC to give the title compound (14 mg), C/MS: m/z 421.0 (M+H), Rt 1.91 min.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-e7c83c6062134cdb85780daf6423935b
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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