Water → HCID 66965069、化合物

HRID 1515002ノート

反応式

HRID 1515002 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6].[CH3:22][O:23][C:24](=[O:37])[CH2:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([CH:34]=O)=[C:29]([CH3:36])[CH:28]=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>CS(C)=O.CCOC(C)=O>[CH3:22][O:23][C:24](=[O:37])[CH2:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([C:34]2[NH:1][C:2]3[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)[CH:18]=[CH:19][C:20]=3[N:21]=2)=[C:29]([CH3:36])[CH:28]=1

参加物

7

反応物 4

HCID 962WaterHCID 2733225Ytterbium triflateHCID 669657403,4-diamino-N-quinolin-2-yl-benzamideHCID 86651272HCID 86651272、化合物

生成物 1

HCID 66965069HCID 66965069、化合物

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3,4-diamino-N-quinolin-2-yl-benzamide (770 mg, 2.77 mmol) and (4-formyl-3,5-dimethylphenoxy)-acetic acid methyl ester (615 mg, 2.77 mmol) in DMSO (10 mL) was added Yb(OTf)3 (344 mg, 0.55 mmol) and the mixture was stirred at ambient temperature overnight. The reaction mixture was partioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (1:4) as eluent gave {3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester as a white solid. MS (m/z) 481.4 (M+1); 1H NMR (Methanol-d4, 400 MHz): δ 8.45 (m, 3H), 8.04 (d, 1H), 7.92 (d, 2H), 7.75 (m, 2H), 7.54 (m, 1H), 6.80 (s, 2H), 4.78 (s, 2H), 3.81 (s, 3H), 2.17 (s, 6H).

後処理

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-390abcac99f44342924c4b424110a8dd
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

反応ノート

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