1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[(1R*,2R*)-2-Aminocyclopentyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride

HRID 2104354ノート

反応式

HRID 2104354 の反応式
[Li+].[CH3:2][N:3]1[CH2:8][CH2:7][C:6]2[N:9]=[C:10]([C:12]([O-:14])=O)[S:11][C:5]=2[CH2:4]1.[ClH:15].CN(C)CCCN=C=NCC.O.O[N:29]1[C:33]2C=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=N1>CN(C)C=O>[ClH:15].[NH2:29][C@@H:33]1[CH2:35][CH2:36][CH2:37][C@H:32]1[NH:31][C:12]([C:10]1[S:11][C:5]2[CH2:4][N:3]([CH3:2])[CH2:8][CH2:7][C:6]=2[N:9]=1)=[O:14]

参加物

5

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23704331Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

生成物 1

HCID 18442877N-[(1R*,2R*)-2-Aminocyclopentyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride収率 96.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The compound obtained in Referential Example 61 (175 mg) was dissolved in N,N-dimethylformamide (3 mL), and to the solution were added 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid lithium salt (90% purity, 258 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (252 mg), 1-hydroxybenzotriazole monohydrate (60 mg), followed by stirring at room temperature for 2 days. The solvent was distilled away under reduced pressure by means of a pump, and the residue was partitioned by adding methylene chloride and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel flash column chromatography (methylene chloride:methanol=47:3). The resultant pale-yellow oily matter was dissolved in hydrochloric acid-ethanol (5 mL), and the solution was stirred at room temperature for 1 hour. Ethyl acetate was added thereto, and the solvent was removed under reduced pressure. Ethyl acetate was added to the residue, and the resultant precipitate was collected by filtration, to thereby give the title compound (120 mg).

後処理

  1. distillationThe solvent was distilled away under reduced pressure by means of a pump
  2. customthe residue was partitioned
  3. additionby adding methylene chloride and saturated aqueous sodium hydrogencarbonate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialwas dried over sodium sulfate anhydrate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue was purified by silica gel flash column chromatography (methylene chloride:methanol=47:3)
  8. dissolutionThe resultant pale-yellow oily matter was dissolved in hydrochloric acid-ethanol (5 mL)
  9. stirringthe solution was stirred at room temperature for 1 hour
  10. additionEthyl acetate was added
  11. customthe solvent was removed under reduced pressure
  12. additionEthyl acetate was added to the residue
  13. filtrationthe resultant precipitate was collected by filtration

出典と根拠

ORDレコード
ord-9a8043d58fe34396ba0a1f2f0608ddba
出典データセット
uspto-grants-2009_08
特許番号
US07576135B2

反応ノート

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