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Acetic Acid → trans 1-(3-amino-cyclopentyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

HRID 906034
ノート
印刷プレビュー

反応式

HRID 906034 の反応式
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@H:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([NH:20][C:21]2[N:22]=[C:23]3[CH:29]=[CH:28][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:24]3=[N:25][CH:26]=2)=[O:19])[CH2:13]1.NN.CC(O)=O>CN(C=O)C>[NH2:3][C@H:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([NH:20][C:21]2[N:22]=[C:23]3[CH:29]=[CH:28][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:24]3=[N:25][CH:26]=2)=[O:19])[CH2:13]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 86642313HCID 86642313、化合物

生成物 1

HCID 67431274trans 1-(3-amino-cyclopentyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea収率 68.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Trans 1-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclopentyl]-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.288 g, 0.50 mmol) was dissolved with heating in DMF (10 mL) and placed in a 45° C. oil bath. The flask was evacuated and refilled with nitrogen three times. Hydrazine (0.16 mL, 5.1 mmol) was added via syringe. After 30 minutes AcOH (0.6 mL) was added and the mixture heated for 30 minutes more before being evaporated. MeOH was added, filtered and the filtrate was evaporated. H2O was added, filtered and the filtrate was evaporated. The residue was purified by reverse phase column chromatography (20-80% MeOH in 0.1% aqueous AcOH) to give trans 1-(3-amino-cyclopentyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.134 g, 60% yield).

後処理

  1. customplaced in a 45° C.
  2. customThe flask was evacuated
  3. additionrefilled with nitrogen three times
  4. temperaturethe mixture heated for 30 minutes more
  5. custombefore being evaporated
  6. additionMeOH was added
  7. filtrationfiltered
  8. customthe filtrate was evaporated
  9. additionH2O was added
  10. filtrationfiltered
  11. customthe filtrate was evaporated
  12. customThe residue was purified by reverse phase column chromatography (20-80% MeOH in 0.1% aqueous AcOH)

出典と根拠

ORDレコード
ord-ecfc1c3f0a6e4aeeb46dbe831b753867
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012974B2

反応ノート

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