Formaldehyde → 1-cyclopropyl-N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamide

HRID 2214513ノート

反応式

HRID 2214513 の反応式
CO[C:3](=[O:20])[C:4]([OH:19])=[CH:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[CH3:8].C=O.C1(N)CC1.ClC1C=C(C=CC=1Cl)CN(C)C([C:35]1C[N:37]([CH3:42])[C:38](=O)[C:39]=1O)=O>>[Cl:17][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[Cl:16])[CH2:9][N:7]([CH3:8])[C:6]([C:5]1[CH2:42][N:37]([CH:38]2[CH2:39][CH2:35]2)[C:3](=[O:20])[C:4]=1[OH:19])=[O:18]

参加物

5

反応物 4

HCID 712FormaldehydeHCID 69828CyclopropylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739、化合物2 回

生成物 1

HCID 546981931-cyclopropyl-N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamide収率 30%

実験手順

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and cyclopropylamine as described in the preparation of Compound 12. The title compound was extracted with EtOAc and the organic layer was washed with H2O, and dried over Na2SO4. After concentration, the resulting residue was triturated with EtOAc/Hexane (1:1) to give a white solid (52.7 mg, 30% yield). Mp=163–164° C. 1H NMR (300 MHz, CDCl3) δ: 9.97 (bs, 1H), 7.42, (d, 1H, J=8.42), 7.35 (s, 1H), 7.10 (dd, 1H, J=8.42, J=1.47), 4.60 (s, 2H), 4.09 (s, 2H), 3.02 (s, 3H), 2.81 (m, 1H), 0.86 (m, 4H). HRMS (M+H) calcd for C16H17N2Cl2O3: 355.0616. found: 355.0618.

後処理

  1. extractionThe title compound was extracted with EtOAc
  2. washthe organic layer was washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe resulting residue was triturated with EtOAc/Hexane (1:1)

出典と根拠

ORDレコード
ord-c4d73387400e411294a19bd49d8c5678
出典データセット
uspto-grants-2006_09
特許番号
US07109186B2

反応ノート

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