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

HRID 731732ノート

反応式

HRID 731732 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0d974e9e231c4025a2ecf542138268e1
出典データセット
uspto-grants-2009_09
特許番号
US07585875B2

反応ノート

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