1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136041777、化合物

HRID 1890479ノート

反応式

HRID 1890479 の反応式
[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O-])=O)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].Cl.[F:20][C:21]1[CH:22]=[C:23]([NH2:32])[C:24]([NH:27][CH2:28][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O.C(O)(=O)C>[F:20][C:21]1[CH:26]=[CH:25][C:24]2[N:27]([CH2:28][CH2:29][O:30][CH3:31])[C:15]([CH2:14][C:9]3[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[N:8]=3)=[N:32][C:23]=2[CH:22]=1

参加物

7

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86762001HCID 86762001、化合物HCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

生成物 1

HCID 136041777HCID 136041777、化合物収率 27%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒

実験手順

The product is prepared according to the procedure described in Example 3, using 300 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 760 mg of 4-fluoro-N1-(2-methoxyethyl)benzene-1,2-diamine hydrochloride and 330 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 5 ml of pyridine and 5 ml of dimethylformamide and then in 5 ml of acetic acid. After refluxing for one hour and purification by silica column chromatography, eluent: CH2Cl2/MeOH: 95/05, the residue obtained is purified by preparative HPLC/MS (method 1). After the acetonitrile has been evaporated off, the pH is brought to 8 using sodium bicarbonate (solid), then the aqueous phase is extracted with twice 25 ml of ethyl acetate, and the combined organic phases are dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure. 120 mg of 2-{[5-fluoro-1-(2-methoxyethyl)-1H-benzimidazol-2-yl]methyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a white powder, the characteristics of which are the following:

後処理

  1. customThe product is prepared
  2. temperatureAfter refluxing for one hour
  3. custompurification by silica column chromatography, eluent
  4. customCH2Cl2/MeOH: 95/05, the residue obtained
  5. customis purified by preparative HPLC/MS (method 1)
  6. customAfter the acetonitrile has been evaporated off
  7. extractionthe aqueous phase is extracted with twice 25 ml of ethyl acetate
  8. dry with materialthe combined organic phases are dried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-e3216039f86c441b96d0c22df5473a3f
出典データセット
uspto-grants-2013_08
特許番号
US08507483B2

反応ノート

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