Furfurylamine → 2-Amino-6-(furfurylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080191노트

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HRID 2080191 반응식
[NH2:1][C:2]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].C1C=CC(CC(NCN[C@H](C(O)=O)CC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1.[CH2:51]([NH2:57])[C:52]1[O:56][CH:55]=[CH:54][CH:53]=1>CS(C)=O.C(N(C(C)C)CC)(C)C.[Cl-].[Na+].O>[NH2:1][C:2]1[N:23]=[C:22]([NH:57][CH2:51][C:52]2[O:56][CH:55]=[CH:54][CH:53]=2)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

참가 물질

7

반응물 3

HCID 3438FurfurylamineHCID 188218A-101HCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

생성물 1

HCID 231305982-Amino-6-(furfurylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide수율 68%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 81531Diisopropylethylamine용매HCID 57417360Sodium chloride; water용매

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온도
135 °C

실험 절차

2-Amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (180 mg, 0.5 mmol) was dissolved in a mixture solution of dimethylsulfoxide (2 mL) and diisopropylethylamine (1 mL), furfurylamine (0.663 mL, 7.5 mmol) was added, and the solution was heated in a sealed tube for 13 hours 30 minutes (oil bath temperature: 135° C.). The reaction mixture was allowed to room temperature, poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1), and the title compound (144 mg, 0.34 mmol, 68%) was obtained.

후처리

  1. additionwas added
  2. customwas allowed to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1)

출처 및 근거

ORD 기록
ord-08831688426e44ab9c30259721c4a998
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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