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Formaldehyde → 1-[(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]piperidin-4-ol

HRID 578756
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HRID 578756 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]=O.[N:10]1[N:11]2[CH:19]=[CH:18][CH:17]=[C:12]2[C:13]([NH2:16])=[N:14][CH:15]=1>C(O)(=O)C>[NH2:16][C:13]1[C:12]2=[CH:17][CH:18]=[C:19]([CH2:8][N:5]3[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]3)[N:11]2[N:10]=[CH:15][N:14]=1
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참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 79341Piperidin-4-olHCID 10441749Pyrrolo[2,1-f][1,2,4]triazin-4-amine

생성물 1

HCID 903891641-[(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]piperidin-4-ol

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

4-Hydroxypiperidine (3.62 g, 35.8 mmol) and 37% formalin solution (2.9 g, 35.8 mmol) were dissolved in acetic acid (150 mL) and stirred at room temperature for 1 h. To this solution was added a solution of pyrrolo[2,1-f][1,2,4]triazin-4-amine (2.0 g, 14.9 mmol; prepared according to the procedure described in WO 2007/056170-A2, Intermediate A) in acetic acid (150 mL), and the mixture was stirred at 60° C. for 2 h. The solvent was then evaporated, and the residue was taken up in 200 mL of half-concentrated aqueous potassium bicarbonate solution and extracted with 200 mL dichloromethane. The organic layer was washed with water (2×50 mL) and discarded. The combined aqueous layers were evaporated to dryness, and the residue was treated with a 10:1 mixture of dichloromethane and methanol (2×100 mL). The organic extracts were evaporated, and the residue was purified by preparative HPLC (method 4) to give 1.16 g (15% of th.) of the title compound.

후처리

  1. customprepared
  2. stirringthe mixture was stirred at 60° C. for 2 h
  3. customThe solvent was then evaporated
  4. extractionextracted with 200 mL dichloromethane
  5. washThe organic layer was washed with water (2×50 mL)
  6. customThe combined aqueous layers were evaporated to dryness
  7. additionthe residue was treated with a 10:1 mixture of dichloromethane and methanol (2×100 mL)
  8. customThe organic extracts were evaporated
  9. customthe residue was purified by preparative HPLC (method 4)

출처 및 근거

ORD 기록
ord-7e7482553e8e4edd8db40ac69c3e3fe9
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040691B2

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