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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Chloroform → 2-({4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-3h,8h-2a,5,8a-triazaacenaphthylene-3,8-dione hydrochloride

HRID 1943200
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HRID 1943200 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=4[N:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.C(Cl)(Cl)[Cl:24].[O:27]1[C:36]2[CH:35]=[C:34]([CH:37]=O)[N:33]=[CH:32][C:31]=2[O:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[ClH:24].[O:27]1[C:36]2[CH:35]=[C:34]([CH2:37][NH:1][CH:2]3[CH2:7][CH2:6][N:5]([CH2:8][CH:9]4[N:19]5[C:20]6[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=6[N:16]=[CH:17][C:18]5=[O:21])[CH2:10]4)[CH2:4][CH2:3]3)[N:33]=[CH:32][C:31]=2[O:30][CH2:29][CH2:28]1
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참가 물질

6

반응물 4

HCID 6212ChloroformHCID 5049666Sodium triacetoxyborohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 580017682-((4-aminopiperidin-1-yl)methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

생성물 1

HCID 685974202-({4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-3h,8h-2a,5,8a-triazaacenaphthylene-3,8-dione hydrochloride
수율 40%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Racemic 2-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (for a preparation see Example 16A(j)) (50 mg, 0.166 mmol) was stirred in 9:1 v:v chloroform:methanol (2 ml) with 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (for a synthesis see WO2004058144 Example 2(c) or WO03/087098 Example 19(d)) (28 mg, 1.0 equivalent) at room temperature for 30 minutes, then the mixture was treated with sodium triacetoxyborohydride (105 mg, 3.0 equivalents) with vigorous stirring. After a further 25 minutes stirring, the reaction was quenched by addition of saturated aqueous sodium hydrogen carbonate (2 ml), diluted with dichloromethane and stirred vigorously at room temperature for 20 minutes. The organic phase was separated (hydrophobic fit) and evaporated under reduced pressure to give an orange gum; this was purified by column chromatography on silica (eluting with 0-12% (2M NH3 in MeOH) in DCM). Appropriate fractions were combined and evaporated under reduced pressure to give the free base of the title compound as a cream amorphous solid (30 mg, 40%).

후처리

  1. customat room temperature
  2. customfor 30 minutes
  3. stirringAfter a further 25 minutes stirring
  4. customthe reaction was quenched by addition of saturated aqueous sodium hydrogen carbonate (2 ml)
  5. additiondiluted with dichloromethane
  6. stirringstirred vigorously at room temperature for 20 minutes
  7. customThe organic phase was separated (hydrophobic fit)
  8. customevaporated under reduced pressure
  9. customto give an orange gum
  10. customthis was purified by column chromatography on silica (eluting with 0-12% (2M NH3 in MeOH) in DCM)
  11. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-77dff1a096614335937e04781b853e6f
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08389524B2

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