Triethylamine → [(E)-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)methylideneamino]urea

HRID 731732노트

반응식

HRID 731732 반응식
[CH:1]([C:4]1[C:12]([CH:13]=O)=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].Cl.[NH2:16][NH:17][C:18]([NH2:20])=[O:19].C(N(CC)CC)C>CO>[CH:1]([C:4]1[C:12](/[CH:13]=[N:16]/[NH:17][C:18]([NH2:20])=[O:19])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 143032672-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde

생성물 1

HCID 57837452[(E)-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)methylideneamino]urea수율 70.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 2-isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde (0.5 g, 1 equivalent), semicarbazide hydrochloride (0.35 g, 1.2 equivalents), and triethylamine (0.4 mL, 1.1 equivalent) in 5 mL of methanol was reflux for 30 minutes. The solution was concentrated and the crude solids produced were extracted with THF, and the mixture was filtered through a 1 inch thick layer of sodium sulfate on top of a thin pad of silica gel to remove the ammonium salt. The filtrate was concentrated and the solid deposited was recrystallized from THF and hexanes to give (E)-2-((2-isopropylpyrazolo[1,5-a]pyridin-3-yl)methylene)hydrazinecarboxamide (0.46 g, 70% yield) as a yellow solid. Compound 1074.

후처리

  1. temperaturewas reflux for 30 minutes
  2. concentrationThe solution was concentrated
  3. customthe crude solids produced
  4. extractionwere extracted with THF
  5. filtrationthe mixture was filtered through a 1 inch thick layer of sodium sulfate on top of a thin pad of silica gel
  6. customto remove the ammonium salt
  7. concentrationThe filtrate was concentrated
  8. customthe solid deposited was recrystallized from THF and hexanes

출처 및 근거

ORD 기록
ord-0d974e9e231c4025a2ecf542138268e1
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585875B2

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