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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
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HRID 906034 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 86642313HCID 86642313, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ecfc1c3f0a6e4aeeb46dbe831b753867
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012974B2

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