1,2-Dichloroethane → (+/-)-6'-[(3-Chlorobenzoyl)amino]-3',4'-dihydro-1'H-spiro[imidazolidine-4,2'-naphthalene]-2,5-dione

HRID 457616Notes

Reaction equation

HRID 457616 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH2:18][C:17]1([C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22]1)[CH2:16][CH2:15]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH2:18][C:17]1([C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22]1)[CH2:16][CH2:15]2)=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 4473-Chlorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 184403106'-Amino-3',4'-dihydrospiro[imidazolidine-4,2'(1'H)-naphthalene]-2,5-dione2×

Product 1

HCID 9820683(+/-)-6'-[(3-Chlorobenzoyl)amino]-3',4'-dihydro-1'H-spiro[imidazolidine-4,2'-naphthalene]-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chlorobenzoic acid (11 mg, 0.067 mmol), (±)-6′-amino-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (described in Intermediate 2) (13 mg, 0.056 mmol), EDC (13 mg, 0.067 mmol), HOBT (10 mg, 0.067 mmol), and N,N-diisopropylethylamine (0.012 mL, 0.067 mmol) was stirred in DMF (0.3 mL) at ambient temperature for 18 h. The crude mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound as a white solid. MS: m/z=370 (M+1). HRMS: m/z=370.0957; calculated m/z=370.0953 for C19H17ClN3O3.

Workup

  1. customThe crude mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-426e7d949744418a84a02614d1161618
Source dataset
uspto-grants-2007_03
Patent number
US07189722B2

Reaction notes

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