Pyridine → 6-Amidino-1-carbamoylmethyl-2-naphthyl 4-[(2-dimethylaminoethyl)aminoiminomethylamino]benzoate

HRID 1419230ノート

反応式

HRID 1419230 の反応式
N1C=CC=CC=1.Cl.Cl.[CH3:9][N:10]([CH3:26])[CH2:11][CH2:12][NH:13][N:14]=[CH:15][NH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1.Cl.[C:28]([C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37]([CH2:41][C:42](=[O:44])[NH2:43])=[C:36](O)[CH:35]=[CH:34]2)(=[NH:30])[NH2:29].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(C(C)=O)C.O.C(O)(=O)C>[CH3:9][N:10]([CH3:26])[CH2:11][CH2:12][NH:13][N:14]=[CH:15][NH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([O:23][C:36]2[CH:35]=[CH:34][C:33]3[C:38](=[CH:39][CH:40]=[C:31]([C:28](=[NH:29])[NH2:30])[CH:32]=3)[C:37]=2[CH2:41][C:42](=[O:44])[NH2:43])=[O:22])=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 1784838554-[(2-Dimethylaminoethyl)aminoiminomethylamino]benzoic acid.dihydrochloride

生成物 1

HCID 1784838546-Amidino-1-carbamoylmethyl-2-naphthyl 4-[(2-dimethylaminoethyl)aminoiminomethylamino]benzoate収率 86.8%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 131721204Methyl ethyl ketone acetic acid water溶媒

実験手順

40 Milliliters of 20% hydrous pyridine was added to 1.5 g of 4-[(2-dimethylaminoethyl)aminoiminomethylamino]benzoic acid.dihydrochloride, 1.03 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 1.44 g of DCC and 56 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours at room temperature. The precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 15 ml of methanol, and this solution was added dropwise to 400 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain a crude product. Then, the product was subjected to silica gel column chromatography using methyl ethyl ketone-water-acetic acid (80:15:5) as an eluent, and the desired fractions were collected and the solvent was distilled off under reduced pressure. To the residue were added 15 ml of methanol and 1.41 ml of concentrated hydrochloric acid, and the solution was added dropwise to 400 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 1.52 g of the desired product.

後処理

  1. temperatureunder cooling with ice
  2. custom24 hours
  3. customat room temperature
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 15 ml of methanol
  7. additionthis solution was added dropwise to 400 ml of acetone
  8. stirringby stirring for 24 hours
  9. temperatureunder cooling with ice
  10. filtrationThen, the precipitate was collected by filtration
  11. customto obtain a crude product
  12. customthe desired fractions were collected
  13. distillationthe solvent was distilled off under reduced pressure
  14. additionTo the residue were added 15 ml of methanol and 1.41 ml of concentrated hydrochloric acid
  15. additionthe solution was added dropwise to 400 ml of acetone
  16. stirringby stirring for 24 hours
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration

出典と根拠

ORDレコード
ord-815d03e3193e49fc8c34386c7dc2c65c
出典データセット
uspto-grants-1999_03
特許番号
US05885990

反応ノート

読み込み中…