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1,2-Dichloroethane → N-(2-((5-(methoxymethyl)furan-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-5-phenyloxazole-4-carboxamide

HRID 82792
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HRID 82792 반응식
N#N.[C:3]1([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([OH:16])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[CH3:40][O:41][CH2:42][C:43]1[O:47][C:46]([CH2:48][N:49]2[N:53]=[C:52]([NH2:54])[CH:51]=[N:50]2)=[CH:45][CH:44]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:40][O:41][CH2:42][C:43]1[O:47][C:46]([CH2:48][N:49]2[N:53]=[C:52]([NH:54][C:14]([C:10]3[N:11]=[CH:12][O:13][C:9]=3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:16])[CH:51]=[N:50]2)=[CH:45][CH:44]=1
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참가 물질

9

반응물 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 679579702-((5-(methoxymethyl)furan-2-yl)methyl)-2H-1,2,3-triazol-4-amine

생성물 1

HCID 86698194
N-(2-((5-(methoxymethyl)furan-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-5-phenyloxazole-4-carboxamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 5-phenyloxazole-4-carboxylic acid (52 mg, 0.26 mmol) in CH2Cl2 (3.0 mL) was treated at rt with DMAP (8.1 mg, 0.07 mmol), HOBt (42.8 mg, 0.32 mmol), EDC (127 mg, 0.66 mmol) and DIPEA (0.2 mL, 1.17 mmol) and the resulting mixture was stirred for 30 min at rt. A solution of 2-((5-(methoxymethyl)furan-2-yl)methyl)-2H-1,2,3-triazol-4-amine (55 mg, 0.26 mmol) in CH2Cl2 (3.0 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (10.0 mL), the layers were separated and the org. phase was washed with water (10.0 mL), followed by brine (10.0 mL) and dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as a colorless oil: TLC: rf (6:4 hept-EA)=0.23. LC-MS-conditions 07: tR=0.87 min, [M+H]+=380.26

후처리

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with water (10.0 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (6:4 hept-EA)

출처 및 근거

ORD 기록
ord-1b883f59590344598efebae03021089f
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846733B2

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