Cyclopropylamine → 2-Amino-cyclopropylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080202노트

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HRID 2080202 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)CC2[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=CC=2)=O)=CC=1.C1(N)CC1>CS(C)=O.C(N(CC)C(C)C)(C)C.[Cl-].[Na+].O>[NH2:1][C:2]1[N:23]=[C:22]([NH:45][CH:42]2[CH2:44][CH2:43]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 69828CyclopropylamineHCID 188218A-101HCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

생성물 1

HCID 231308022-Amino-cyclopropylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide수율 47.5%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 81531Diisopropylethylamine용매HCID 57417360Sodium chloride; water용매

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온도
130 °C

실험 절차

2-Amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (30 mg, 0.083 mmol) was dissolved in a mixture solution of dimethylsulfoxide (1 mL) and N,N-diisopropylethylamine (0.5 mL), cyclopropylamine (0.058 mL, 0.84 mmol) was added thereto, followed by heating in a sealed tube for 15 hours 30 minutes (oil bath temperature: 130° C.). The reaction mixture was allowed to room temperature, poured into brine, which was then 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 (15 mg, 0.039 mmol, 47.5%) was obtained.

후처리

  1. additionwas added
  2. customwas allowed to room temperature
  3. extractionwas then 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-10b4597d1c894627866eb85a8509fa9d
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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