Triethylamine → 2,6-Diamino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-nicotinamide

HRID 1171183노트

반응식

HRID 1171183 반응식
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[C:14]([CH2:16][NH2:17])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[N:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>O.CS(C)=O>[NH2:20][C:21]1[N:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:22]=1[C:23]([NH:17][CH2:16][C:14]1[O:15][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:19]=[CH:18][C:12]=2[CH:13]=1)=[O:24]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189772452,6-Diaminonicotinic acidHCID 57608217C-(6-Benzyloxybenzofuran-2-yl)-methylamine

생성물 1

HCID 119608292,6-Diamino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-nicotinamide수율 60%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a dimethylsulfoxide (10 mL) solution of C-(6-benzyloxy-benzofuran-2-yl)-methylamine (300 mg, 1.18 mmol) described in Production Example 1-2-4 were added 2,6-diaminonicotinic acid (181 mg) described in Production Example 1-1-4, 1-hydroxybenzotriazole (319 mg, 2.36 mmol), triethylamine (329 μL, 2.36 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (452 mg, 2.36 mmol) at room temperature, which was stirred at room temperature for 26 hours. To the reaction solution was added water at room temperature followed by extracting with ethyl acetate. After washing the organic layer with water and sat. NaCl, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (227 mg, 60%) as a white solid.

후처리

  1. extractionby extracting with ethyl acetate
  2. washAfter washing the organic layer with water and sat. NaCl
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-72337d5db5274d7785a46a73ca47aa09
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829585B2

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