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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,6-Diaminopyridine-3-carboxamide

HRID 1927227
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HRID 1927227 반응식
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:14]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>O.CS(C)=O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:14])=[O:5]
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참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 189772452,6-Diaminonicotinic acid

생성물 1

HCID 204748872,6-Diaminopyridine-3-carboxamide수율 73.8%

시약·촉매·용매

2
HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

2,6-Diaminonicotinic acid (1.5 g), WSC (2.8 g), HOBt (2.0 g), ammonium chloride (1.6 g), diisopropylethylamine (7.6 g), and DMSO (45 mL) were stirred for 15 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated and purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol=4:1). The organic layer thus obtained was concentrated and purified by NH silica gel column chromatography (ethyl acetate). Ethyl acetate and hexane were added to the residue thus obtained, and the solids were filtered off to obtain the titled compound (1.1 g).

후처리

  1. extractionwas then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography (ethyl acetate
  4. customThe organic layer thus obtained
  5. concentrationwas concentrated
  6. custompurified by NH silica gel column chromatography (ethyl acetate)
  7. additionEthyl acetate and hexane were added to the residue
  8. customthus obtained
  9. filtrationthe solids were filtered off

출처 및 근거

ORD 기록
ord-01050031bd7d42c6ae7a0e2674aca124
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183264B2

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