1,2-Dichloroethane → (+/-)-2,5-Dioxo-N-(quinolin-8-ylmethyl)-3',4'-dihydro-1'H-spiro[imidazolidine-4,2'-naphthalene]-6'-carboxamide

HRID 1182220Notes

Reaction equation

HRID 1182220 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.[C:13]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH2:22][C:21]1([C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26]1)[CH2:20][CH2:19]2)(O)=[O:14].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[O:31]=[C:27]1[NH:26][C:21]2([CH2:20][CH2:19][C:18]3[C:23](=[CH:24][CH:25]=[C:16]([C:13]([NH:1][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[C:7]5[C:12]=4[N:11]=[CH:10][CH:9]=[CH:8]5)=[O:14])[CH:17]=3)[CH2:22]2)[C:29](=[O:30])[NH:28]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 15079229(Quinolin-8-yl)methanamineHCID 18440314(+/-)-6'-carboxy-3',4'-dihydro-1'H-spiro[imidazolidine-4,2'-naphthalene]-2,5-dione2×

Product 1

HCID 9843928(+/-)-2,5-Dioxo-N-(quinolin-8-ylmethyl)-3',4'-dihydro-1'H-spiro[imidazolidine-4,2'-naphthalene]-6'-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-(aminomethyl)quinoline (14 mg, 0.088 mmol), (±)-6′-carboxy-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (described in Intermediate 1) (15 mg, 0.058 mmol), EDC (22 mg, 0.115 mmol), and HOBT (13 mg, 0.088 mmol) was stirred in DMF (0.8 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 tan solid. MS: m/z=401 (M+1). HRMS: m/z=401.1584; calculated m/z=401.1608 for C23H21N4O3.

Workup

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

Sources & evidence

ORD record
ord-c3ddfab5def74c78bed521de474c432f
Source dataset
uspto-grants-2007_10
Patent number
US07288559B2

Reaction notes

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