Ethyl Acetate → [3-(4-Methyl-5-pyridin-4-yl-thiazol-2-yl)-ureido]-acetic acid ethyl ester

HRID 1951182ノート

反応式

HRID 1951182 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([NH2:13])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:15]=[O:16].C(OCC)(=O)C>CN(C=O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][NH:14][C:15]([NH:13][C:4]1[S:5][C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:2]([CH3:1])[N:3]=1)=[O:16])[CH3:22]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 76283Ethyl isocyanatoacetateHCID 201450032-Amino-4-methyl-5-(pyridin-4-yl)thiazole

生成物 1

HCID 11415948[3-(4-Methyl-5-pyridin-4-yl-thiazol-2-yl)-ureido]-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of 4-methyl-5-pyridin-4-yl-thiazol-2-ylamine (prepared according to the method described in European patent specification EP 117082 A2) (0.068 g, 3.56 mmol) in DMF (5 ml) is treated with ethyl isocyanatoacetate (0.043 ml, 3.916 mmol) and the solution is stirred overnight. The solvent is removed in vacuo and the crude product is partitioned between ethyl acetate (50 ml) and water (50 ml). The layers are separated and the aqueous portion is extracted with ethyl acetate (2×50 ml). The combined organic portions are washed with water, dried (MgSO4), filtered and concentrated in vacuo to yield an oil. Trituration with ethyl acetate yields the titled compound.

後処理

  1. customThe solvent is removed in vacuo
  2. customthe crude product is partitioned between ethyl acetate (50 ml) and water (50 ml)
  3. customThe layers are separated
  4. extractionthe aqueous portion is extracted with ethyl acetate (2×50 ml)
  5. washThe combined organic portions are washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield an oil

出典と根拠

ORDレコード
ord-98792d835a804a5c965c91f49bb395a7
出典データセット
uspto-grants-2013_03
特許番号
US08404684B2

反応ノート

読み込み中…