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

HRID 1182220ノート

反応式

HRID 1182220 の反応式
[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

参加物

6

反応物 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 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c3ddfab5def74c78bed521de474c432f
出典データセット
uspto-grants-2007_10
特許番号
US07288559B2

反応ノート

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